Tricyclic compounds and PBK inhibitors containing the same

ABSTRACT

Tricyclic compounds are provided. These compounds are PBK inhibitors, and are useful for the treatment of PBK related diseases, including cancer.

PRIORITY

The present application is a U.S. National Phase Application of PCT/US2011/030278, filed Mar. 29, 2011, which claims the benefit of U.S. Provisional Application No. 61/318,606, filed on Mar. 29, 2010, the contents of each of which are hereby incorporated herein by reference in their entirety for all purposes.

TECHNICAL FIELD

The present invention relates to a compound for inhibiting PBK activity, a method for the preparation thereof, and a pharmaceutical composition containing the compound as an active ingredient.

BACKGROUND ART

Previous studies revealed that PDZ binding kinase (PBK) is a serine/threonine kinase related to the dual specific mitogen-activated protein kinase kinase (MAPKK) family (Abe Y, et al., J Biol. Chem. 275: 21525-21531, 2000, Gaudet S, et al., Proc Natl Acad. Sci. 97: 5167-5172, 2000 and Matsumoto S, et al., Biochem Biophys Res Commun. 325: 997-1004, 2004). PBK was also indicated to be involved in mitosis as shown by its significant role in highly proliferating spermatocytes (Gaudet S, et al., Proc Natl Acad. Sci. 97: 5167-5172, 2000 and Fujibuchi T, et al., Dev Growth Differ. 47:637-44, 2005). In fact, abundant expression of PBK was observed in testis, while almost no PBK expression was detected in other normal organs (Park J H, et al., Cancer Res. 66: 9186-95, 2006). PBK regulates cell cycle progression. In accordance with this, its significant overexpression was detected in clinical breast cancer samples (Park J H, et al., Cancer Res. 66: 9186-95, 2006), Burkitt's lymphoma (Simons-Evelyn M, et al., Blood Cells Mol Dis. 27: 825-829, 2001) and a variety of hematologic malignancies (Nandi A, et al., Blood Cells Mol Dis. 32: 240-5, 2004).

Immunohistochemical analysis of testis revealed the expression of PBK protein around the outer region of seminiferous tubules where repeated mitosis of sperm germ cells followed by meiosis occurs (Fujibuchi T, et al., Dev Growth Differ. 47: 637-44, 2005). Especially, at prophase and metaphase, the subcellular localization of PBK was detected around the condensed chromosome in breast cancer cells (Park J H, et al., Cancer Res. 66: 9186-95, 2006). Moreover the knockdown of PBK expression with gene specific siRNAs caused dysfunction of cytokinesis and subsequently led to apoptosis of the cancer cells (Park J H, et al., Cancer Res. 66: 9186-95, 2006). These indicated the critical function of PBK at mitosis, in testicular and cancer cells.

Taken together, PBK-specific inhibitors can be used as a drug applicable for a broad spectrum of cancers. PBK is an excellent target for cancer therapy for the following reasons: i) almost no expression in normal organs (except for testis); ii) frequent overexpression in clinical cancer samples; iii) a serine/threonine kinase related to the essential function for cell mitosis.

The present inventors have found that a Tricyclic compound can selectively inhibit the activity of PBK.

SUMMARY OF INVENTION

Accordingly, it is an object of the present invention to provide a PBK inhibitor having high inhibitory activity against PBK.

It is another object of the present invention to provide a method for preparing such inhibitor.

It is a further object of the present invention to provide a pharmaceutical composition including the compound, a pharmaceutically acceptable salt, hydrate, solvate, or isomer thereof.

In accordance with one aspect of the present invention, there is provided a compound of formula (I), and a pharmaceutically acceptable salt, hydrate, solvate, or isomer thereof:

A compound represented by general formula I:

or a pharmaceutically acceptable salt thereof, wherein R¹, R², R³, and R⁴ are each independently a group selected from the group consisting of: hydrogen, hydroxyl, halogen, cyano, nitro, amino, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₁-C₆ alkoxy, C₆-C₁₀ aryl, indanyl, heteroaryl, 3- to 8-membered heterocycloalkyl, —OSO₂CH₃, —OSO₂CF₃, and —CONH₂, wherein each of the groups of R¹ to R⁴ is optionally substituted with a substituent selected from the group consisting of substituent A below: substituent A:

-   -   hydroxyl;     -   oxo (═O);     -   cyano;     -   halogen;     -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally substituted         with a substituent selected from the group consisting of         substituent B below);     -   C₃-C₁₀ cycloalkyl [wherein the C₃-C₁₀ cycloalkyl is optionally         substituted with cyano, or C₁-C₆ alkyl substituted with —NR³¹R³²         (wherein R³¹ and R³² each independently represent hydrogen or         C₁-C₆ alkyl)];     -   —NR²¹R²² [wherein R²¹ and R²² each independently represent         hydrogen, or C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally         substituted with di(C₁-C₆ alkyl)amino, C₁-C₆ alkylsulfonyl         (—SO₂(C₁-C₆ alkyl)), or 3- to 8-membered heterocycloalkyl)];     -   C₁-C₆ alkoxy {wherein the C₁-C₆ alkoxy is optionally substituted         with halogen, 3- to 8-membered heterocycloalkyl (wherein the 3-         to 8-membered heterocycloalkyl is optionally substituted with         C₁-C₆ alkyl), or —NR³³R³⁴ [wherein R³³ and R³⁴ each         independently represent hydrogen, C₁-C₆ alkyl (wherein the C₁-C₆         alkyl is optionally substituted with C₁-C₆ alkylsulfonyl or         di(C₁-C₆ alkyl)amino), or C₁-C₆ alkylsulfonyl]};     -   —SO₂NR²³R²⁴ {wherein R²³ and R²⁴ each independently represent         hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is optionally         substituted with hydroxyl, C₁-C₆ alkoxy, halogen, C₃-C₁₀         cycloalkyl, or —NR³⁵R³⁶ (wherein R³⁵ and R³⁶ each independently         represent hydrogen or C₁-C₆ alkyl)], C₃-C₁₀ cycloalkyl (wherein         the C₃-C₁₀ cycloalkyl is optionally substituted with C₁-C₆         hydroxyalkyl), or 3- to 8-membered heterocycloalkyl; or R²³ and         R²⁴ may together form 3- to 8-membered heterocycloalkyl wherein         the 3- to 8-membered heterocycloalkyl is optionally substituted         with amino};     -   C₁-C₆ alkylsulfonyl (wherein the C₁-C₆ alkyl moiety is         optionally substituted with hydroxyl);     -   C₁-C₆ alkylsulfonylamino (—NHSO₂(C₁-C₆ alkyl)) [wherein the         C₁-C₆ alkyl moiety is optionally substituted with —NR³⁷R³⁸         (wherein R³⁷ and R³⁸ each independently represent hydrogen or         C₁-C₆ alkyl)];     -   3- to 8-membered heterocycloalkyl {wherein the 3- to 8-membered         heterocycloalkyl is optionally substituted with —NR³⁹R⁴⁰         (wherein R³⁹ and R⁴⁰ each independently represent hydrogen,         C₁-C₆ alkyl, or C₁-C₆ alkylsulfonyl), C₁-C₆ alkyl [wherein the         C₁-C₆ alkyl is optionally substituted with —NR⁴¹R⁴² (wherein R⁴¹         and R⁴² each independently represent hydrogen or C₁-C₆ alkyl)],         hydroxyl, or C₁-C₆ alkylsulfonyl};     -   heteroaryl;     -   —COOR¹¹ (wherein R¹¹ represents hydrogen or C₁-C₆ alkyl); and     -   —COR¹² [wherein R¹² represents C₁-C₆ alkyl, C₃-C₁₀ cycloalkyl,         cyanomethyl, —NR²⁵R²⁶ {wherein R²⁵ and R²⁶ each independently         represent hydrogen, or C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is         optionally substituted with hydroxyl or —NR⁴³R⁴⁴ (wherein R⁴³         and R⁴⁴ each independently represent hydrogen or C₁-C₆ alkyl)]},         or 3- to 8-membered heterocycloalkyl which is optionally         substituted with C₁-C₆ alkyl],         substituent B:     -   halogen;     -   hydroxyl;     -   cyano;     -   3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered         heterocycloalkyl is optionally substituted with C₁-C₆ alkyl,         hydroxyl, amino, C₁-C₆ aminoalkyl, or C₁-C₆ alkyl substituted         with C₂-C₇ alkyloxycarbonylamino);     -   —NR⁵¹R⁵² {wherein R⁵¹ and R⁵² each independently represent         hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is optionally         substituted with C₁-C₆ alkylsulfonyl, or 3- to 8-membered         heterocycloalkyl optionally substituted with —COOR⁵³ (wherein         R⁵³ represents hydrogen or C₁-C₆ alkyl)], 3- to 8-membered         heterocycloalkyl, C₁-C₆ alkylsulfonyl, C₃-C₁₀ cycloalkyl, —COR⁵⁵         (wherein R⁵⁵ represents C₁-C₆ alkyl), —COOR⁵⁶ (wherein R⁵⁶         represents C₁-C₆ alkyl), or —CONR⁵⁷R⁵⁸ (wherein R⁵⁷ and R⁵⁸ each         independently represent hydrogen or C₁-C₆ alkyl)}; and     -   —COOR⁵⁴ (wherein R⁵⁴ represents hydrogen or C₁-C₆ alkyl)];         wherein R⁵ is hydrogen or C₁-C₆ alkyl; and         wherein

is a structure selected from the group consisting of

-   -   (i) —S—CR⁷═CR⁶—,     -   (ii) —CH₂—CH₂—CH₂—,     -   (iii) —NH—CH═CCH₃—, and     -   (iv) —N═CH—S—,         wherein R⁶ is     -   hydrogen,     -   hydroxyl,     -   C₁-C₆ alkyl,     -   C₆-C₁₀ aryl (wherein the C₆-C₁₀ aryl is optionally substituted         with hydroxyl), or 3- to 8-membered heterocycloalkyl [wherein         the 3- to 8-membered heterocycloalkyl is optionally substituted         with —NR⁶¹R⁶² (wherein R⁶¹ and R⁶² each independently represent         hydrogen or C₁-C₆ alkyl)], and         wherein R⁷ is     -   hydrogen,     -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally substituted         with hydroxyl, —NR⁷¹R⁷² [wherein R⁷¹ and R⁷² each independently         represent hydrogen, C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is         optionally substituted with dimethylamino), C₃-C₁₀ cycloalkyl         (wherein the C₃-C₁₀ cycloalkyl is optionally substituted with         amino), or 3- to 8-membered heterocycloalkyl], or 3- to         8-membered heterocycloalkyl (wherein the 3- to 8-membered         heterocycloalkyl is optionally substituted with C₁-C₆         aminoalkyl)),     -   C₆-C₁₀ aryl (wherein the C₆-C₁₀ aryl is optionally substituted         with hydroxyl), or     -   —COR⁷³ {wherein R⁷³ represents 3- to 8-membered heterocycloalkyl         (wherein the 3- to 8-membered heterocycloalkyl is optionally         substituted with amino), or —NR⁷⁴R⁷⁵ [wherein R⁷⁴ and R⁷⁵ each         independently represent hydrogen, 3- to 8-membered         heterocycloalkyl, or C₃-C₁₀ cycloalkyl (wherein the C₃-C₁₀         cycloalkyl is optionally substituted with amino)]}.

It must be noted that as used in the specification and in the appended claims, the singular forms “a”, “an”, and “the” include plural reference unless the context clearly dictates otherwise. Thus, for example, reference to “a group” is a reference to one or more groups.

DESCRIPTION OF EMBODIMENTS

In this invention, “alkyl” group refers to a straight chain or a branched chain hydrocarbon group which does not contain any hetero atoms or unsaturated carbon-carbon bonds. “C₁-C₆ alkyl” refers to an alkyl group which has 1-6 carbon atom(s). “C₁-C₄ alkyl” refers to an alkyl group which has 1-4 carbon atom(s).

Examples of “C1-C6 alkyl” include, but are not limited to, methyl, ethyl, 1-propyl, 2-propyl, 2-methyl-1-propyl, 2-methyl-2-propyl(tert-butyl(1,1-dimethyl-ethyl), 1-butyl, 2-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2,2-dimethyl-1-butyl, 2-ethyl-1-butyl, 3,3-dimethyl-2-butyl, and 2,3-dimethyl-2-butyl.

In this invention, “alkenyl” group refers to a straight chain or a branched chain hydrocarbon group which contains one or more than one unsaturated carbon-carbon bond(s) and does not contain any hetero atoms. “C₂-C₆ alkenyl” refers to an alkenyl group which has 2-6 carbon atoms.

Examples of “C₂-C₆ alkenyl” include, but are not limited to, vinyl(ethenyl), 1-propenyl, 2-propenyl, 3-propenyl, 2-methyl-prop-1-en-1-yl(2-methyl-1-propenyl), 2-methyl-prop-1-en-3-yl(2-methyl-2-propenyl), but-1-en-1-yl, but-1-en-2-yl, but-1-en-3-yl, but-2-en-1-yl, but-2-en-2-yl, pent-1-en-1-yl, pent-1-en-2-yl, pent-1-en-3-yl, pent-1-en-4-yl, pent-1-en-5-yl, pent-2-en-1-yl, pent-2-en-2-yl, pent-2-en-3-yl(1-ethyl-1-propenyl), pent-2-en-4-yl, pent-2-en-5-yl, 2-methyl-but-1-en-1-yl, 2-methyl-but-1-en-2-yl, 2-methyl-but-1-en-3-yl, 2-methyl-but-1-en-4-yl, 2-methyl-but-2-en-1-yl, 2-methyl-but-2-en-3-yl, 2-methyl-but-2-en-4-yl, 3-methyl-but-1-en-1-yl, 3-methyl-but-1-en-2-yl, 3-methyl-but-1-en-3-yl, 3-methyl-but-1-en-4-yl, 2,2-dimethyl-prop-1-en-1-yl, 2,2-dimethyl-prop-1-en-2-yl, hex-1-en-1-yl, hex-1-en-2-yl, hex-1-en-3-yl, hex-1-en-4-yl, hex-1-en-5-yl, hex-1-en-6-yl, hex-2-en-1-yl, hex-2-en-2-yl, hex-2-en-3-yl, hex-2-en-4-yl, hex-2-en-5-yl, hex-2-en-6-yl, hex-3-en-1-yl, hex-3-en-2-yl, hex-3-en-3-yl, 2-methyl-pent-1-en-1-yl, 2-methyl-pent-1-en-3-yl, 2-methyl-pent-1-en-4-yl, 2-methyl-pent-1-en-5-yl, 2-methyl-pent-2-en-1-yl, 2-methyl-pent-2-en-3-yl, 2-methyl-pent-2-en-4-yl, 2-methyl-pent-2-en-5-yl, 3-methyl-pent-1-en-1-yl, 3-methyl-pent-1-en-2-yl, 3-methyl-pent-1-en-3-yl, 3-methyl-pent-1-en-4-yl, 3-methyl-pent-1-en-5-yl, 3-methyl-pent-2-en-1-yl, 3-methyl-pent-2-en-2-yl, 3-methyl-pent-2-en-4-yl, 3-methyl-pent-2-en-5-yl, 4-methyl-pent-1-en-1-yl, 4-methyl-pent-1-en-2-yl, 4-methyl-pent-1-en-3-yl, 4-methyl-pent-1-en-4-yl, 4-methyl-pent-1-en-5-yl, 4-methyl-pent-2-en-1-yl, 4-methyl-pent-2-en-2-yl, 4-methyl-pent-2-en-3-yl, 4-methyl-pent-2-en-4-yl, 4-methyl-pent-2-en-5-yl, 2,3-dimethyl-but-1-en-1-yl, 2,3-dimethyl-but-1-en-3-yl, 2,3-dimethyl-but-1-en-4-yl, 2,3-dimethyl-but-2-en-1-yl, 3,3-dimethyl-but-1-en-1-yl, 3,3-dimethyl-but-1-en-2-yl, 3,3-dimethyl-but-1-en-4-yl, 2-ethyl-but-1-en-1-yl, 2-ethyl-but-1-en-3-yl, 2-ethyl-but-1-en-4-yl, 3-ethyl-but-1-en-1-yl, 3-ethyl-but-1-en-2-yl, 3-ethyl-but-1-en-3-yl, 3-ethyl-but-1-en-4-yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-2-en-3-yl and 2-ethyl-but-2-en-4-yl.

In this invention, “alkynyl” group refers to a straight chain or a branched chain hydrocarbon group which contains at least one triple carbon-carbon bond and does not contain any hetero atoms. “C₂-C₆ alkynyl” refers to an alkynyl group which has 2-6 carbon atoms.

Examples of “C₂-C₆ alkynyl” include, but are not limited to, ethinyl, 1-propinyl, 2-propinyl, 3-propinyl, 2-methyl-prop-1-in-1-yl, 2-methyl-prop-1-in-3-yl, but-1-in-1-yl, but-1-in-2-yl, but-1-in-3-yl, but-2-in-1-yl, but-2-in-2-yl, pent-1-in-1-yl, pent-1-in-2-yl, pent-1-in-3-yl, pent-1-in-4-yl, pent-1-in-5-yl, pent-2-in-1-yl, pent-2-in-2-yl, pent-2-in-3-yl, pent-2-in-4-yl, pent-2-in-5-yl, 2-methyl-but-1-in-1-yl, 2-methyl-but-1-in-2-yl, 2-methyl-but-1-in-3-yl, 2-methyl-but-1-in-4-yl, 2-methyl-but-2-in-1-yl, 2-methyl-but-2-in-3-yl, 2-methyl-but-2-in-4-yl, 3-methyl-but-1-in-1-yl, 3-methyl-but-1-in-2-yl, 3-methyl-but-1-in-3-yl, 3-methyl-but-1-in-4-yl, 2,2-dimethyl-prop-1-in-1-yl, 2,2-dimethyl-prop-1-in-2-yl, hex-1-in-1-yl, hex-1-in-2-yl, hex-1-in-3-yl, hex-1-in-4-yl, hex-1-in-5-yl, hex-1-in-6-yl, hex-2-in-1-yl, hex-2-in-2-yl, hex-2-in-3-yl, hex-2-in-4-yl, hex-2-in-5-yl, hex-2-in-6-yl, hex-3-in-1-yl, hex-3-in-2-yl, hex-3-in-3-yl, 2-methyl-pent-1-in-1-yl, 2-methyl-pent-1-in-3-yl, 2-methyl-pent-1-in-4-yl, 2-methyl-pent-1-in-5-yl, 2-methyl-pent-2-in-1-yl, 2-methyl-pent-2-in-3-yl, 2-methyl-pent-2-in-4-yl, 2-methyl-pent-2-in-5-yl, 3-methyl-pent-1-in-1-yl, 3-methyl-pent-1-in-2-yl, 3-methyl-pent-1-in-3-yl, 3-methyl-pent-1-in-4-yl, 3-methyl-pent-1-in-5-yl, 3-methyl-pent-2-in-1-yl, 3-methyl-pent-2-in-2-yl, 3-methyl-pent-2-in-4-yl, 3-methyl-pent-2-in-5-yl, 4-methyl-pent-1-in-1-yl, 4-methyl-pent-1-in-2-yl, 4-methyl-pent-1-in-3-yl, 4-methyl-pent-1-in-4-yl, 4-methyl-pent-1-in-5-yl, 4-methyl-pent-2-in-1-yl, 4-methyl-pent-2-in-2-yl, 4-methyl-pent-2-in-3-yl, 4-methyl-pent-2-in-4-yl, 4-methyl-pent-2-in-5-yl, 2,3-dimethyl-but-1-in-1-yl, 2,3-dimethyl-but-1-in-3-yl, 2,3-dimethyl-but-1-in-4-yl, 2,3-dimethyl-but-2-in-1-yl, 3,3-dimethyl-but-1-in-1-yl, 3,3-dimethyl-but-1-in-2-yl, 3,3-dimethyl-but-1-in-4-yl, 2-ethyl-but-1-in-1-yl, 2-ethyl-but-1-in-3-yl, 2-ethyl-but-1-in-4-yl, 3-ethyl-but-1-in-1-yl, 3-ethyl-but-1-in-2-yl, 3-ethyl-but-1-in-3-yl, 3-ethyl-but-1-in-4-yl, 2-ethyl-but-2-in-1-yl, 2-ethyl-but-2-in-3-yl and 2-ethyl-but-2-in-4-yl.

In the present invention, “alkoxy” group refers to a group represented by —OR, wherein R is alkyl.

“C₁-C₆ alkoxy” group refers to an alkoxy group which has 1-6 carbon atom(s). “C₁-C₄ alkoxy” refers to an alkoxy group which has 1-4 carbon atom(s).

Examples of “C₁-C₆ alkoxy” include, but are not limited to, methoxy, ethoxy, 1-propyloxy, 2-propyloxy, 2-methyl-1-propyloxy, 2-methyl-2-propyloxy, and 1-butyloxy, and 2-butyloxy.

In the present invention, “cycloalkyl” group refers to a saturated carbon ring system. “C₃-C₁₀ cycloalkyl” group refers to 3-10 membered cycloalkyl.

Examples of “C₃-C₁₀ cycloalkyl” include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptanyl, cyclooctanyl, and adamantyl. For example, 3-8 membered cycloalkyl is also included in “C₃-C₁₀ cycloalkyl”.

In the present invention, “C₃-C₁₀cycloalkenyl” group refers to a cyclic unsaturated aliphatic hydrocarbon group of 3 to 10 carbon atoms with at least one double bond (two adjacent SP² carbon atoms).

Specific examples of “C₃-C₁₀cycloalkenyl” include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and cyclooctenyl.

In the present invention, “C₆-C₁₀aryl” refers to an aromatic cyclic hydrocarbon group of 6 to 10 carbon atoms.

Specific examples of “C₆-C₁₀aryl” include phenyl, 1-naphthyl, and 2-naphthyl.

In the present invention, “halogen” refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

As used herein, “hetero atom” refers to a sulfur atom, an oxygen atom, or a nitrogen atom.

In this invention, “amino” refers to a group represented by —NH₂ whose hydrogens may each be optionally substituted by a substituent.

In the present invention, “C₁-C₆ alkylamino” refers to an amino group bound to the C₁-C₆ alkyl.

Examples of “C₁-C₆ alkylamino” include, but are not limited to, methylamino, ethylamino, propylamino, isopropylamino, n-butylamino, s-butylamino, t-butylamino, and 2-ethylbutylamino.

In the present invention, “di(C₁-C₆alkyl)amino” refers to an amino group bound to two “C₁-C₆alkyls” defined above.

Specific examples of “di(C₁-C₆alkyl)amino” include dimethylamino, diethylamino, dipropylamino, diisopropylamino, di-n-butylamino, di-s-butylamino, di-t-butylamino, and di-2-ethylbutylamino.

In the present invention, “C₂-C₇alkyloxycarbonylamino” refers to a group represented by (C₁-C₆alkyl)-O—C═O—NH—, or a group in which the “C₁-C₆alkyl” defined above is bound to —OCONH—.

In the present invention, “C₁-C₆aminoalkyl” refers to a group in which an amino group is bound to the “C₁-C₆alkyl” defined above.

In the present invention, “C₁-C₆hydroxyalkyl” refers to a group in which one or more hydroxy groups are bound to the “C₁-C₆alkyl” defined above.

In this invention, “sulfonyl” is a group represented by —SO₂—.

In this invention, “C₁-C₆ alkylsulfonyl” refers to R—SO₂— wherein R is the C₁-C₆ alkyl. “C₁-C₄ alkylsulfonyl” refers to R—SO₂— wherein R is C₁-C₄ alkyl.

Examples of “C₁-C₆ alkylsulfonyl” include, but are not limited to, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, t-butylsulfonyl, and 2-ethylbutylsulfonyl.

In this invention, “C₆-C₁₀ arylsulfonyl” refers to R—SO₂— wherein R is the C₆-C₁₀ aryl.

Examples of “C₆-C₁₀ arylsulfonyl” include, but are not limited to, phenylsulfonyl.

In the present invention, “C₁-C₆alkylsulfonylamino” refers to R—SO₂—NH— wherein R is “C₁-C₆ alkyl”. “C₁-C₄ alkylsulfonylamino” refers to R—SO₂—NH— wherein R is R—SO₂—NH— wherein R is “C₁-C₄ alkyl”.

Examples of “C₁-C₆ alkylsulfonylamino” include, but are not limited to, methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, isopropylsulfonylamino, n-butylsulfonylamino, s-butylsulfonylamino, t-butylsulfonylamino, and 2-ethylbutylsulfonylamino.

In this invention, “sulfinyl” is a group represented by —SO—.

In this invention, “C₁-C₆ alkylsulfinyl” refers to R—SO— wherein R is the C₁-C₆ alkyl. “C₁-C₄ alkylsulfinyl” refers to R—SO— wherein R is C₁-C₄ alkyl.

Examples of “C₁-C₆ alkylsulfinyl” include, but are not limited to, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, and 2-ethylbutylsulfinyl.

In the present invention, “heteroaryl” refers to a monocyclic or fused aromatic heterocyclic group that includes at least one hetero atom selected from O, S, and N. When the aromatic heterocyclic group is a fused ring, those including a partially hydrogenated ring are also included in “heteroaryl”.

Examples of such heteroaryls include pyrazolyl, thiazolyl, isothiazolyl, thiadiazolyl, imidazolyl, furyl, thienyl, oxazolyl, isooxazolyl, pyrrolyl, imidazolyl, (1,2,3)- and (1,2,4)-triazolyl, tetrazolyl, pyranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, tetrahydroisoquinolyl, benzofuranyl, isobenzofuranyl, indolynyl, indolyl, isoindolyl, indazolyl, benzoimidazolyl, benzotriazolyl, benzooxazolyl, benzothiazolyl, benzo[b]thiophenyl, (1,2)- and (1,3)-benzooxathiol, chromenyl, 2-oxochromenyl, benzothiadiazolyl, quinolizinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, tetrahydroisoquinolyl, tetrazolyl, [1,2,4]triazo[1.5-a]pyridyl, 1H-pyrrolo[2,3-b]pyridyl, and 2,3-dihydrobenzooxazolyl.

Preferable examples include pyrazolyl, furyl, thienyl, pyridyl, pyrimidinyl, tetrahydroisoquinolyl, indolynyl, indazolyl, benzoimidazolyl, benzooxazolyl, tetrahydroisoquinolyl, tetrazolyl, [1,2,4]triazo[1.5-a]pyridyl, 1H-pyrrolo[2,3-b]pyridyl, and 2,3-dihydrobenzooxazolyl.

In the present invention, “3- to 8-membered heterocycloalkyl” refers to a non-aromatic monovalent 3- to 8-membered ring that includes 1 to 3 hetero atoms in the atoms forming the ring, and that may have a double bond within the ring.

Examples of “3- to 8-membered heterocycloalkyl” include aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, azepanyl, morpholinyl, oxetanyl, and 1,2,5,6-tetrahydropyridyl.

A salt is defined as the product formed from the neutralisation reaction of acids and bases. Salts are ionic compounds composed of cations (positively charged ions) and anions (negative ions) so that the product is electrically neutral. These component ions can be inorganic as well as organic.

Hydrate is a term used in inorganic chemistry and organic chemistry to indicate that a substance contains water. Solvate refers to a molecule in a solution complexed by solvent molecules. Isomers are compounds with the same molecular formula but different structural formulae. More specifically, isomer includes geometric isomer, optical isomer, stereoisomer, tautomer of the compound, and mixtures thereof.

In a preferred embodiments, the present invention provides [1] a compound represented by formula (I) or a pharmaceutically acceptable salt thereof:

-   -   or a pharmaceutically acceptable salt thereof,     -   wherein R¹, R², R³, and R⁴ are each independently a group         selected from the group consisting of:     -   hydrogen,     -   hydroxyl,     -   halogen,     -   cyano,     -   nitro,     -   amino,     -   C₁-C₆ alkyl,     -   C₂-C₆ alkenyl,     -   C₂-C₆ alkynyl,     -   C₃-C₁₀ cycloalkyl,     -   C₃-C₁₀ cycloalkenyl,     -   C₁-C₆ alkoxy,     -   C₆-C₁₀ aryl,     -   indanyl,     -   heteroaryl,     -   3- to 8-membered heterocycloalkyl,     -   —OSO₂CH₃,     -   —OSO₂CF₃,     -   —CONH₂,     -   —OCONR¹⁰¹R¹⁰², wherein R¹⁰¹ and R¹⁰² each independently is         hydrogen, C₁-C₆ alkyl, or R¹⁰¹ and R¹⁰² taken together form         morpholinyl,     -   —OCOR¹⁰³, wherein R¹⁰³ represents C₁-C₆ alkyl, and     -   —OCOOR¹⁰⁴, wherein R¹⁰⁴ represents C₁-C₆ alkyl,     -   wherein R¹, R², R³, and R⁴ are optionally substituted with a         substituent independently selected from the group consisting of         substituent A;     -   wherein substituent A is independently selected from the group         consisting of:         -   hydroxyl;         -   oxo (═O);         -   cyano;         -   halogen;         -   C₁-C₆ alkyl optionally substituted with substituent B;         -   C₃-C₁₀ cycloalkyl optionally substituted with cyano or C₁-C₆             alkyl substituted with —NR³¹R³², wherein R³¹ and R³² each             independently represent hydrogen or C₁-C₆ alkyl;         -   —NR²¹R²², wherein R²¹ and R²² each independently represent             hydrogen; C₁-C₆ alkyl optionally substituted with hydroxyl,             amino, di(C₁-C₆ alkyl)amino, —SO₂(C₁-C₆ alkyl), 3- to             8-membered heterocycloalkyl, or cyano; or a 3- to 8-membered             heterocycloalkyl optionally substituted with —COOR¹⁰⁵             wherein R¹⁰⁵ represents C₁-C₆ alkyl;         -   C₁-C₆ alkoxy optionally substituted with halogen, 3- to             8-membered heterocycloalkyl optionally substituted with             C₁-C₆ alkyl, or —NR³³R³⁴ wherein R³³ and R³⁴ each             independently represent hydrogen, C₁-C₆ alkylsulfonyl, or             C₁-C₆ alkyl optionally substituted with C₁-C₆ alkylsulfonyl             or di(C₁-C₆ alkyl)amino;         -   —SO₂NR²³R²⁴, wherein R²³ and R²⁴ each independently             represent hydrogen; C₁-C₆ alkyl optionally substituted with             hydroxyl, C₁-C₆ alkoxy, halogen, C₃-C₁₀ cycloalkyl,             heteroaryl, or —NR³⁵R³⁶ wherein R³⁵ and R³⁶ each             independently represent hydrogen or C₁-C₆ alkyl; C₃-C₁₀             cycloalkyl optionally substituted with C₁-C₆ hydroxyalkyl;             3- to 8-membered heterocycloalkyl; or R²³ and R²⁴ taken             together form 3- to 8-membered heterocycloalkyl optionally             substituted with amino or halogen;         -   C₁-C₆ alkylsulfonyl optionally substituted with hydroxyl;         -   —NHSO₂(C₁-C₆ alkyl), wherein the carbon atoms are optionally             substituted with —NR³⁷R³⁸ wherein R³⁷ and R³⁸ each             independently represent hydrogen or C₁-C₆ alkyl;         -   3- to 8-membered heterocycloalkyl optionally substituted             with —NR³⁹R⁴⁰, wherein R³⁹ and R⁴⁰ each independently             represent hydrogen, C₁-C₆ alkyl, or C₁-C₆ alkylsulfonyl;             C₁-C₆ alkyl optionally substituted with —NR⁴¹R⁴², wherein             R⁴¹ and R⁴² each independently represent hydrogen or C₁-C₆             alkyl; hydroxyl; or C₁-C₆ alkylsulfonyl;         -   aryl optionally substituted with C₁-C₆ alkyl optionally             substituted with cyano or amino;         -   heteroaryl;         -   —COOR¹¹, wherein R¹¹ represents hydrogen or C₁-C₆ alkyl; and         -   —COR¹², wherein R¹² represents C₁-C₆ alkyl; C₃-C₁₀             cycloalkyl; cyanomethyl; aminomethyl; —NR²⁵R²⁶ wherein R²⁵             and R²⁶ each independently represent hydrogen or C₁-C₆ alkyl             optionally substituted with hydroxyl or —NR⁴³R⁴⁴, wherein             R⁴³ and R⁴⁴ each independently represent hydrogen or C₁-C₆             alkyl; or 3- to 8-membered heterocycloalkyl optionally             substituted with C₁-C₆ alkyl;     -   wherein substituent B is independently selected from the group         consisting of:         -   halogen;         -   hydroxyl;         -   C₁-C₆ alkoxy;         -   cyano;         -   cycloalkyl;         -   C₆-C₁₀ aryl optionally substituted with cyano;         -   heteroaryl;         -   3- to 8-membered heterocycloalkyl optionally substituted             with C₁-C₆ alkyl, hydroxyl, amino, C₁-C₆ aminoalkyl, or             C₁-C₆ alkyl substituted with C₂-C₇ alkyloxycarbonylamino;         -   —NR⁵¹R⁵², wherein R⁵¹ and R⁵² each independently represent             hydrogen; C₁-C₆ alkyl optionally substituted with C₁-C₆             alkylsulfonyl or 3- to 8-membered heterocycloalkyl             optionally substituted with —COOR⁵⁶ wherein R⁵³ represents             hydrogen or C₁-C₆ alkyl; 3- to 8-membered heterocycloalkyl;             C₁-C₆ alkylsulfonyl; C₃-C₁₀ cycloalkyl; —COR⁵⁵ wherein R⁵⁵             represents C₁-C₆ alkyl; —COOR⁵⁶ wherein R⁵⁶ represents C₁-C₆             alkyl; or —CONR⁵⁷R⁵⁸ wherein R⁵⁷ and R⁵⁸ each independently             represent hydrogen or C₁-C₆ alkyl;         -   —COOR⁵⁴, wherein R⁵⁴ represents hydrogen or C₁-C₆ alkyl;         -   —CONH₂;         -   —SO₂NR¹⁰⁶R¹⁰⁷, wherein R¹⁰⁶ and R¹⁰⁷ each independently             represent hydrogen, C₁-C₆ alkyl, or C₃-C₁₀ cycloalkyl;         -   C₁-C₆ alkylsulfinyl; and         -   C₁-C₆ alkylsulfonyl;     -   wherein R⁵ is hydrogen or C₁-C₆ alkyl; and     -   wherein

-   -    is a structure selected from the group consisting of         -   (i) —S—CR⁷═CR⁶—,         -   (ii) —CH₂—CH₂—CH₂—,         -   (iii) —NR¹⁰⁸—CH═CR¹⁰⁹—, wherein R¹⁰⁸ represents hydrogen, or             C₁-C₆ alkyl optionally substituted with hydroxyl, and R¹⁰⁹             represents hydrogen, CH₃, or phenyl substituted with C₁-C₆             aminoalkyl, and         -   (iv) —N═CH—S—,     -   wherein R⁶ is selected from the group consisting of:         -   hydrogen,         -   hydroxyl,         -   C₁-C₆ alkyl,         -   C₆-C₁₀ aryl optionally substituted with hydroxyl, and         -   3- to 8-membered heterocycloalkyl optionally substituted             with —NR⁶¹R⁶², wherein R⁶¹ and R⁶² each independently             represent hydrogen or C₁-C₆ alkyl;     -   wherein R⁷ is selected from the group consisting of:         -   hydrogen;         -   halogen;         -   C₁-C₆ alkyl optionally substituted with hydroxyl, —NR⁷¹R⁷²             wherein R⁷¹ and R⁷² each independently represent hydrogen;             C₁-C₆ alkyl optionally substituted with dimethylamino;             C₃-C₁₀ cycloalkyl optionally substituted with amino or 3- to             8-membered heterocycloalkyl; or 3- to 8-membered             heterocycloalkyl optionally substituted with C₁-C₆             aminoalkyl;         -   C₆-C₁₀ aryl optionally substituted with hydroxyl;         -   C₆-C₁₀ arylsulfonyl; and         -   —COR⁷³, wherein R⁷³ represents 3- to 8-membered             heterocycloalkyl optionally substituted with amino; or             —NR⁷⁴R⁷⁵ wherein R⁷⁴ and R⁷⁵ each independently represent             hydrogen, 3- to 8-membered heterocycloalkyl, or C₃-C₁₀             cycloalkyl optionally substituted with amino.

-   [2] The compound of [1], or a pharmaceutically acceptable salt     thereof, wherein

-    is —S—CR⁷═CR⁶—. -   [3] The compound of [2], or a pharmaceutically acceptable salt     thereof, wherein R¹ is hydrogen, cyano, C₁-C₆ alkyl optionally     substituted with hydroxyl or halogen, C₃-C₁₀ cycloalkyl, C₂-C₆     alkenyl, C₂-C₆ alkynyl, or halogen. -   [4] The compound of [2], or a pharmaceutically acceptable salt     thereof, wherein R² is hydrogen, hydroxyl, halogen, C₁-C₆ alkoxy, or     C₆-C₁₀ aryl optionally substituted with hydroxyl. -   [5] The compound of [2] or a pharmaceutically acceptable salt,     wherein R² is hydrogen, hydroxyl, halogen, C₁-C₆ alkoxy, or     dihydroxyphenyl. -   [6] The compound of [2], or a pharmaceutically acceptable salt     thereof, wherein R³ is selected from the group consisting of:     hydrogen; hydroxyl; C₁-C₆ alkyl optionally substituted with     hydroxyl, halogen, or hydroxyethylamino; halogen; C₁-C₆ alkoxy     optionally substituted with dimethylamino or morpholinyl; C₁-C₆     alkylphenyl, wherein the aliphatic carbons are optionally     substituted with —NR⁵¹R⁵²; cyano; nitro; amino; 3- to 8-membered     heterocycloalkyl optionally substituted with amino; heteroaryl;     —OSO₂CH₃; —OSO₂CF₃; —OCOR¹⁰³, wherein R¹⁰³ represents C₁-C₆ alkyl;     —OCOOR¹⁰⁴ wherein R¹⁰⁴ represents C₁-C₆ alkyl; —OCONR¹⁰¹R¹⁰²²     wherein R¹⁰¹ and R¹⁰² each independently represent hydrogen or C₁-C₆     alkyl, or R¹⁰¹ and R¹⁰² taken together form morpholinyl; and —CONH₂. -   [7] The compound of [6], or a pharmaceutically acceptable salt     thereof, wherein when R³ is a 3- to 8-membered heterocycloalkyl, the     3- to 8-membered heterocycloalkyl is selected from the group     consisting of piperidyl, pyrrolidinyl, morpholinyl, or piperazinyl     and optionally substituted with amino; and when R³ is heteroaryl,     the heteroaryl is pyridyl. -   [8]. The compound of [2], or a pharmaceutically acceptable salt     thereof, wherein R⁴ is selected from the group consisting of     hydrogen, hydroxyl, halogen, amino, C₁-C₆ alkyl, C₂-C₆ alkenyl,     C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₁-C₆ alkoxy, C₆-C₁₀ aryl,     indanyl, heteroaryl, and 3- to 8-membered heterocycloalkyl, and R⁴     is optionally substituted with substituent A. -   [9] The compound of [8], or a pharmaceutically acceptable salt     thereof, wherein when R⁴ is heteroaryl, the heteroaryl is selected     from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl,     [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl,     2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl,     pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl);     and wherein the 3- to 8-membered heterocycloalkyl is selected from     the group consisting of aziridinyl, azetidinyl, pyrrolidinyl,     imidazolidinyl, piperidyl, piperazinyl, azepanyl, morpholinyl, and     1,2,3,6-tetrahydropyridyl; wherein each of the groups of R⁴ is     optionally substituted with substituent A-1;     -   wherein substituent A-1 is selected from the group consisting         of:     -   hydroxyl;     -   oxo;     -   cyano;     -   halogen;     -   C₁-C₆ alkyl optionally substituted with a substituent selected         from the group consisting of substituent B-1;     -   C₃-C₁₀ cycloalkyl optionally substituted with cyano, or C₁-C₆         alkyl substituted with —NR³¹R³²;     -   —NR^(21A)R^(22A), wherein R^(21A) and R^(22A) each independently         represent hydrogen; C₁-C₆ alkyl optionally substituted with         amino, di(C₁-C₆ alkyl)amino, —SO₂ (C₁-C₆ alkyl), piperidyl, or         cyano; or piperidyl optionally substituted with —COOR¹⁰⁵;     -   C₁-C₆ alkoxy optionally substituted with halogen; a 3- to         8-membered heterocycloalkyl selected from piperidyl and         piperazinyl, either of which is optionally substituted with         C₁-C₆ alkyl; or —NR³³R³⁴;     -   —SO₂NR^(23A)R^(24A), wherein R^(23A) and R^(24A) each         independently represent hydrogen, C₁-C₆ alkyl optionally         substituted with hydroxyl, C₁-C₆ alkoxy, halogen, C₃-C₁₀         cycloalkyl, pyrazolyl, imidazolyl, or —NR³⁵R³⁶; C₃-C₁₀         cycloalkyl optionally substituted with C₁-C₆ hydroxyalkyl;         azetidinyl; pyrrolidinyl, or R^(23A) and R^(24A) taken together         form pyrrolidinyl optionally substituted with amino or halogen;     -   C₁-C₆ alkylsulfonyl optionally substituted with hydroxyl;     -   —NHSO₂(C₁-C₆ alkyl), wherein the carbon atoms are optionally         substituted with NR³⁷R³⁸;     -   3- to 8-membered heterocycloalkyl selected from the group         consisting of azetidinyl, pyrrolidinyl, piperidyl, piperazinyl,         and tetrahydropyridyl any of which is optionally substituted         with —NR³⁹R⁴⁰; C₁-C₆ alkyl optionally substituted with —NR⁴¹R⁴²;         hydroxyl; or C₁-C₆ alkylsulfonyl;     -   1H-tetrazolyl;     -   aryl optionally substituted with C₁-C₆ alkyl, wherein C₁-C₆ is         the aliphatic carbons are optionally substituted with cyano or         amino;     -   —COOR¹¹; and     -   —COR^(12A), wherein R^(12A) represents piperazinyl optionally         substituted with C₁-C₆ alkyl; C₃-C₁₀ cycloalkyl; cyanomethyl;         aminomethyl; —NR²⁵R²⁶ wherein R²⁵ and R²⁶ each independently         represent hydrogen or C₁-C₆ alkyl optionally substituted with         hydroxyl or —NR⁴³R⁴⁴; or C₁-C₆ alkylsulfonyl;     -   wherein substituent B-1 is selected from the group consisting         of:     -   halogen;     -   hydroxyl;     -   C₁-C₆ alkoxy;     -   cyano;     -   cycloalkyl;     -   phenyl optionally substituted with cyano;     -   heteroaryl selected from the group consisting of imidazolyl,         pyrazolyl, and thiazolyl;     -   3- to 8-membered heterocycloalkyl selected from the group         consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl,         and oxetanyl any of which are optionally substituted with         hydroxyl, amino, C₁-C₆ aminoalkyl, or C₁-C₆ alkyl optionally         substituted with C₂-C₇ alkyloxycarbonylamino;     -   —NR^(51A)R^(52A), wherein R^(51A) and R^(52A) each independently         represent hydrogen; C₁-C₆ alkyl optionally substituted with         C₁-C₆ alkylsulfonyl or piperidyl optionally substituted with         —COOR⁵³; piperidyl; C₁-C₆ alkylsulfonyl; C₃-C₁₀ cycloalkyl;         —COR⁵⁵, —COOR⁵⁶, or —CONR⁵⁷R⁵⁸;     -   —COOR⁵⁴;     -   —CONH₂;     -   —SO₂NR¹⁰⁶R¹⁰⁷;     -   C₁-C₆ alkylsulfinyl; and     -   C₁-C₆ alkylysulfonyl. -   [10] The compound of [9], or a pharmaceutically acceptable salt     thereof, wherein R⁴ is a group selected from group (p):     -   wherein group (p) is independently selected from the group         consisting of:         -   hydrogen,         -   hydroxyl,         -   halogen,         -   amino optionally substituted with a substituent selected             from the group consisting of substituent (g),         -   C₁-C₆ alkyl optionally substituted with a substituent             selected from the group consisting of substituent (a),         -   C₂-C₆ alkenyl optionally substituted with a substituent             selected from the group consisting of substituent (b),         -   C₃-C₁₀ cycloalkyl,         -   C₃-C₁₀ cycloalkenyl,         -   C₁-C₆ alkoxy,         -   C₆-C₁₀ aryl optionally substituted with a substituent             selected from the group consisting of substituent (c),         -   indanyl optionally substituted with a substituent selected             from the group consisting of substituent (d),         -   heteroaryl selected from the group consisting of pyridyl,             1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl,             benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl,             pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl,             thienyl, and tetrahydroisoquinolyl any of which is             optionally substituted with a substituent selected from the             group consisting of substituent (e); and         -   3- to 8-membered heterocycloalkyl selected from the group             consisting of pyrrolidinyl, piperidyl, piperazinyl,             morpholinyl, and 1,2,3,6-tetrahydropyridyl any of which is             optionally substituted with a substituent selected from the             group consisting of substituent (f);         -   wherein substituent (a) is selected from the group             consisting of:             -   —NR^(21A)R^(22A), wherein R^(21A) and R^(22A) each                 independently represent hydrogen; C₁-C₆ alkyl optionally                 substituted with piperidyl; or piperidyl optionally                 substituted with —COOR¹⁰⁵;             -   3- to 8-membered heterocycloalkyl selected from the                 group consisting of pyrrolidinyl and piperidyl either of                 which is optionally substituted with C₁-C₆ alkyl                 optionally substituted with —NR⁴¹R⁴² or —NR³⁹R⁴⁰ wherein                 R³⁹ and R⁴ each independently represent hydrogen or                 C₁-C₆ alkyl; and             -   —NHSO₂(C₁-C₆ alkyl);         -   wherein substituent (b) is selected from the group             consisting of:             -   —COOR¹¹;             -   —NR^(21a)R^(22a), wherein R^(21a) and R^(22a) each                 independently represent hydrogen, or C₁-C₆ alkyl                 optionally substituted with di(C₁-C₆ alkyl)amino or                 C₁-C₆ alkylsulfonyl;             -   3- to 8-membered heterocycloalkyl selected from the                 group consisting of azetidinyl, pyrrolidinyl, and                 piperidyl any of which are optionally substituted with                 —NR³⁹R⁴⁰, C₁-C₆ alkyl optionally substituted with                 —NR⁴¹R⁴², hydroxyl, or C₁-C₆ alkylsulfonyl;             -   cyano; and             -   C₁-C₆ alkoxy;         -   wherein substituent (c) is selected from the group             consisting of:             -   hydroxyl;             -   cyano;             -   halogen;             -   C₁-C₆ alkyl optionally substituted with a substituent                 selected from the group consisting of substituent B-c                 below;             -   C₃-C₁₀ cycloalkyl optionally substituted with cyano, or                 C₁-C₆ alkyl substituted with —NR³¹R³²;             -   —NR^(21c)R^(22c), wherein R^(21c) and R^(22c) each                 independently represent hydrogen or C₁-C₆ alkyl                 optionally substituted with amino or cyano;             -   C₁-C₆ alkoxy optionally substituted with halogen, 3- to                 8-membered heterocycloalkyl selected from the group                 consisting of piperidyl and piperazinyl either of which                 are optionally substituted with C₁-C₆ alkyl, or                 —NR³³R³⁴;             -   —SO₂NR^(23c)R^(24c), wherein R^(23c) and R^(24c) each                 independently represent hydrogen, C₁-C₆ alkyl optionally                 substituted with hydroxyl, C₁-C₆ alkoxy, halogen, C₃-C₁₀                 cycloalkyl, pyrazolyl, imidazolyl, or —NR³⁵R³⁶; C₃-C₁₀                 cycloalkyl optionally substituted with C₁-C₆                 hydroxyalkyl; azetidinyl, pyrrolidinyl, or wherein                 R^(23c) and R^(24c) taken together form pyrrolidinyl                 which is optionally substituted with amino or halogen;             -   C₁-C₆ alkylsulfonyl optionally substituted with                 hydroxyl;             -   —NHSO₂(C₁-C₆ alkyl), wherein the carbon atoms are                 optionally substituted with NR³⁷R³⁸;             -   piperazinyl optionally substituted with C₁-C₆ alkyl or                 C₁-C₆ alkylsulfonyl;             -   piperidyl optionally substituted with hydroxyl;             -   1H-tetrazolyl;             -   1,2,3,6-tetrahydropyridyl; and             -   —COR^(12c), wherein R^(12c) represents piperazinyl which                 is optionally substituted with C₁-C₆ alkyl, C₃-C₁₀                 cycloalkyl, cyanomethyl, aminomethyl, —NR²⁵R²⁶, or C₁-C₆                 alkyl; and         -   wherein substituent B-c is selected from the group             consisting of:             -   halogen;             -   hydroxyl;             -   methoxy;             -   cyano;             -   C₃-C₁₀ cycloalkyl;             -   3- to 8-membered heterocycloalkyl selected from the                 group consisting of pyrrolidinyl, piperidyl,                 piperazinyl, morpholinyl, and oxetanyl, any of which is                 optionally substituted with C₁-C₆ alkyl, hydroxyl,                 amino, C₁-C₆ aminoalkyl, or C₁-C₆ alkyl substituted with                 C₂-C₇ alkyloxycarbonylamino;             -   —NR^(51c)R^(52c), wherein R^(51c) and R^(52c) each                 independently represent hydrogen; C₁-C₆ alkyl optionally                 substituted with C₁-C₆ alkylsulfonyl, or piperidyl                 optionally substituted with —COOR⁵³; piperidyl;                 C₁-C₆alkylsulfonyl; C₃-C₁₀ cycloalkyl; —COR⁵⁵; or                 —CONR⁵⁷R⁵⁸;             -   heteroaryl selected from the group consisting of                 imidazolyl, pyrazolyl, and thiazolyl;             -   —COOR⁵⁴;             -   —CONH₂;             -   —SO₂NR¹⁰⁶R¹⁰⁷;             -   C₁-C₆ alkylsufinyl; and             -   C₁-C₆ alkylsulfonyl;         -   wherein substituent (d) is selected from the group             consisting of:             -   —NR^(21d)R^(22d), wherein R^(21d) and R^(22d) each                 independently represent hydrogen or C₁-C₆ alkyl;         -   wherein substituent (e) is selected from the group             consisting of:             -   hydroxyl;             -   oxo;             -   cyano;             -   C₃-C₁₀ cycloalkyl optionally substituted with cyano;             -   —NR^(21e)R^(22e), wherein R^(21e) and R^(22e) each                 independently represent hydrogen or C₁-C₆ alkyl                 optionally substituted with amino;             -   piperidyl;             -   C₁-C₆ alkoxy optionally substituted with —NR³³R³⁴;             -   C₁-C₆ alkyl optionally substituted with cyano;                 —NR^(51e)R^(52e), wherein R^(51e) and R^(52e) each                 independently represent hydrogen, C₁-C₆ alkyl, or                 —COOR⁵⁶; morpholinyl; or cyanophenyl;             -   —CONH₂;         -   wherein substituent (f) is selected from the group             consisting of:             -   C₁-C₆ alkyl optionally substituted with                 —NR^(51f)R^(52f), wherein R^(51f) and R^(52f) each                 independently represent hydrogen, C₁-C₆ alkyl, or                 —COOR⁵⁶; and C₁-C₆ alkylsulfonyl;         -   wherein substituent (g) is aryl optionally substituted with             C₁-C₆ alkyl having the aliphatic carbons optionally             substituted with cyano or amino. -   [11] The compound of [2], or a pharmaceutically acceptable salt     thereof, wherein R⁶ is hydrogen; hydroxyl; C₁-C₆ alkyl; phenyl     optionally substituted with 1 to 3 hydroxyls; piperidyl optionally     substituted with amino; or piperazinyl. -   [12] The compound of [11], or a pharmaceutically acceptable salt     thereof, wherein R⁷ is hydrogen; C₁-C₆ alkyl optionally substituted     with hydroxyl or piperidyl; or halogen. -   [13] The compound of [2], or a pharmaceutically acceptable salt     thereof, wherein R⁷ is hydrogen;     -   C₁-C₆ alkyl optionally substituted with hydroxyl;         —NR^(71A)R^(72A) wherein R^(71A) and R^(72A) independently         represent hydrogen, C₁-C₆ alkyl optionally substituted with         dimethylamino, C₃-C₁₀ cycloalkyl optionally substituted with         amino, or piperidyl; or 3- to 8-membered heterocycloalkyl         selected from the group consisting of piperidyl and morpholinyl         either of which is optionally substituted with C₁-C₆ aminoalkyl;     -   phenyl optionally substituted with 1 to 2 hydroxyls;     -   phenylsulfonyl; or     -   —COR^(73A), wherein R^(73A) represents piperidyl optionally         substituted with amino, or —NR^(74A)R^(75A), wherein R^(74A) and         R^(75A) each independently represent hydrogen, piperidyl, or         C₃-C₁₀ cycloalkyl optionally substituted with amino. -   [14] The compound of [1], or a pharmaceutically acceptable salt     thereof, wherein

-    is —CH₂—CH₂—CH₂—. -   [15] The compound of [14], or a pharmaceutically acceptable salt     thereof, wherein R¹ and R² are hydrogen. -   [16] The compound of [14], or a pharmaceutically acceptable salt     thereof, wherein R³ is hydroxyl or methoxy. -   [17] The compound of [14], or a pharmaceutically acceptable salt     thereof, wherein R⁴ is hydrogen; phenyl substituted with C₁-C₆ alkyl     substituted with —NR^(51A)R^(52A), wherein R^(51A) and R^(52A) each     independently represent hydrogen or C₁-C₆ alkyl, or     —SO₂NR^(53A)R^(54A), wherein R^(53A) and R^(54A) each independently     represent hydrogen or C₁-C₆ alkyl optionally substituted with     halogen or hydroxy; 1,2,3,6-tetrahydropyridyl; hydroxypyridyl; or     methoxypyridyl. -   [18] The compound of [1], or a pharmaceutically acceptable salt     thereof, wherein

-    is —NR¹⁰⁸—CH═CR¹⁰⁹—,     -   R¹, R², and R⁴ are hydrogen, and     -   R³ is hydrogen, hydroxyl or C₁-C₆ alkoxy. -   [19] The compound of [1], or a pharmaceutically acceptable salt     thereof, wherein

-    is —N═CH—S—,     -   R¹, R², and R⁴ are hydrogen, and     -   R³ is methoxy.

Alternatively, in some embodiments, the present invention also provides a compound represented by formula (I) or a pharmaceutically acceptable salt thereof:

-   1. A compound represented by general formula I:

-   -   or a pharmaceutically acceptable salt thereof,     -   wherein R¹, R², R³, and R⁴ are each independently a group         selected from the group consisting of:     -   hydrogen,     -   hydroxyl,     -   halogen,     -   cyano,     -   nitro,     -   amino,     -   C₁-C₆ alkyl,     -   C₂-C₆ alkenyl,     -   C₂-C₆ alkynyl,     -   C₃-C₁₀ cycloalkyl,     -   C₃-C₁₀ cycloalkenyl,     -   C₁-C₆ alkoxy,     -   C₆-C₁₀ aryl,     -   indanyl,     -   heteroaryl,     -   3- to 8-membered heterocycloalkyl,     -   —OSO₂CH₃,     -   —OSO₂CF₃,     -   —CONH₂     -   —OCONR¹⁰¹R¹⁰² (wherein R¹⁰¹ and R¹⁰² each independently         represent hydrogen or C₁-C₆ alkyl, or R¹⁰¹ and R¹⁰² together         form morpholinyl),     -   —OCOR¹⁰³ (wherein R¹⁰³ represents C₁-C₆ alkyl), and     -   —OCOOR¹⁰⁴ (wherein R¹⁰⁴ represents C₁-C₆ alkyl)     -   wherein each of the groups of R¹ to R⁴ is optionally substituted         with a substituent selected from the group consisting of         substituent A below:     -   substituent A:         -   hydroxyl;         -   oxo (═O);         -   cyano;         -   halogen;         -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally             substituted with a substituent selected from the group             consisting of substituent B below);         -   C₃-C₁₀ cycloalkyl [wherein the C₃-C₁₀ cycloalkyl is             optionally substituted with cyano, or C₁-C₆ alkyl             substituted with —NR³¹R³² (wherein R³¹ and R³² each             independently represent hydrogen or C₁-C₆ alkyl)];         -   —NR²¹R²² [wherein R²¹ and R²² each independently represent             hydrogen, C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally             substituted with hydroxyl, amino, di(C₁-C₆ alkyl)amino,             C₁-C₆ alkylsulfonyl (—SO₂(C₁-C₆ alkyl)), 3- to 8-membered             heterocycloalkyl, or cyano), or 3- to 8-membered             heterocycloalkyl (wherein the 3- to 8-membered             heterocycloalkyl is optionally substituted with —COOR¹⁰⁵             (wherein R¹⁰⁵ represents C₁-C₆))];         -   C₁-C₆ alkoxy {wherein the C₁-C₆ alkoxy is optionally             substituted with halogen, 3- to 8-membered heterocycloalkyl             (wherein the 3- to 8-membered heterocycloalkyl is optionally             substituted with C₁-C₆ alkyl), or —NR³³R³⁴ [wherein R³³ and             R³⁴ each independently represent hydrogen, C₁-C₆ alkyl             (wherein the C₁-C₆ alkyl is optionally substituted with             C₁-C₆ alkylsulfonyl or di(C₁-C₆ alkyl)amino), or C₁-C₆             alkylsulfonyl]};         -   —SO₂NR²³R²⁴ (wherein R²³ and R²⁴ each independently             represent hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is             optionally substituted with hydroxyl, C₁-C₆ alkoxy, halogen,             C₃-C₁₀ cycloalkyl, heteroaryl, or —NR³⁵R³⁶ (wherein R³⁵ and             R³⁶ each independently represent hydrogen or C₁-C₆ alkyl)],             C₃-C₁₀ cycloalkyl (wherein the C₃-C₁₀ cycloalkyl is             optionally substituted with C₁-C₆ hydroxyalkyl), or 3- to             8-membered heterocycloalkyl; or R²³ and R²⁴ may together             form 3- to 8-membered heterocycloalkyl wherein the 3- to             8-membered heterocycloalkyl is optionally substituted with             amino or halogen);         -   C₁-C₆ alkylsulfonyl (wherein the C₁-C₆ alkyl moiety is             optionally substituted with hydroxyl);         -   C₁-C₆ alkylsulfonylamino (—NHSO₂(C₁-C₆ alkyl)) [wherein the             C₁-C₆ alkyl moiety is optionally substituted with —NR³⁷R³⁸             (wherein R³⁷ and R³⁸ each independently represent hydrogen             or C₁-C₆ alkyl)];         -   3- to 8-membered heterocycloalkyl (wherein the 3- to             8-membered heterocycloalkyl is optionally substituted with             —NR³⁹R⁴⁰ (wherein R³⁹ and R⁴⁰ each independently represent             hydrogen, C₁-C₆ alkyl, or C₁-C₆ alkylsulfonyl), C₁-C₆ alkyl             [wherein the C₁-C₆ alkyl is optionally substituted with             —NR⁴¹R⁴² (wherein R⁴¹ and R⁴² each independently represent             hydrogen or C₁-C₆ alkyl)], hydroxyl, or C₁-C₆             alkylsulfonyl);         -   Aryl (wherein the aryl is optionally substituted with C₁-C₆             alkyl[wherein C₁-C₆ alkyl is optionally substituted with             cyano or amino]);         -   heteroaryl;         -   —COOR¹¹ (wherein R¹¹ represents hydrogen or C₁-C₆ alkyl);             and         -   —COR¹² [wherein R¹² represents C₁-C₆ alkyl, C₃-C₁₀             cycloalkyl, cyanomethyl, aminomethyl, —NR²⁵R²⁶ {wherein R²⁵             and R²⁶ each independently represent hydrogen, or C₁-C₆             alkyl [wherein the C₁-C₆ alkyl is optionally substituted             with hydroxyl or —NR⁴³R⁴⁴ (wherein R⁴³ and R⁴⁴ each             independently represent hydrogen or C₁-C₆ alkyl)]}), or 3-             to 8-membered heterocycloalkyl which is optionally             substituted with C₁-C₆ alkyl],     -   substituent B:         -   halogen;         -   hydroxyl;         -   C₁-C₆ alkoxy;         -   cyano;         -   cycloalkyl;         -   C₆-C₁₀ aryl (wherein C₆-C₁₀ aryl is optionally substituted             with cyano) heteroaryl;         -   3- to 8-membered heterocycloalkyl (wherein the 3- to             8-membered heterocycloalkyl is optionally substituted with             C₁-C₆ alkyl, hydroxyl, amino, C₁-C₆ aminoalkyl, or C₁-C₆             alkyl substituted with C₂-C₇ alkyloxycarbonylamino);         -   —NR⁵¹R⁵² {wherein R⁵¹ and R⁵² each independently represent             hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is optionally             substituted with C₁-C₆ alkylsulfonyl, or 3- to 8-membered             heterocycloalkyl optionally substituted with —COOR⁵³             (wherein R⁵³ represents hydrogen or C₁-C₆ alkyl)], 3- to             8-membered heterocycloalkyl, C₁-C₆ alkylsulfonyl, C₃-C₁₀             cycloalkyl, —COR⁵⁵ (wherein R⁵⁵ represents C₁-C₆ alkyl),             —COOR⁵⁶ (wherein R⁵⁶ represents C₁-C₆ alkyl), or —CONR⁵⁷R⁵⁸             (wherein R⁵⁷ and R⁵⁸ each independently represent hydrogen             or C₁-C₆ alkyl)};         -   —COOR⁵⁴ (wherein R⁵⁴ represents hydrogen or C₁-C₆ alkyl)];         -   —CONH₂;         -   —SO₂NR¹⁰⁶R¹⁰⁷ (wherein R¹⁰⁶ and R¹⁰⁷ each independently             represent hydrogen, C₁-C₆ alkyl, or C₃-C₁₀ cycloalkyl)         -   C₁-C₆ alkylsulfinyl; and         -   C₁-C₆ alkylsulfonyl;     -   wherein R⁵ is hydrogen or C₁-C₆ alkyl; and     -   wherein

-   -    is a structure selected from the group consisting of         -   (i) —S—CR⁷═CR⁶—,         -   (ii)-CH₂—CH₂—CH₂—,         -   (iii)-NR¹⁰⁸—CH═CR¹⁰⁹— (wherein R¹⁰⁸ represents hydrogen, or             C₁-C₆ alkyl that is optionally substituted with hydroxyl,             and R¹⁰⁹ represents hydrogen, CH₃, or phenyl that is             substituted with C₁-C₆ aminoalkyl, and         -   (iv) —N═CH—S—,     -   wherein R⁶ is         -   hydrogen,         -   hydroxyl,         -   C₁-C₆ alkyl,         -   C₆-C₁₀ aryl (wherein the C₆-C₁₀ aryl is optionally             substituted with hydroxyl), or         -   3- to 8-membered heterocycloalkyl [wherein the 3- to             8-membered heterocycloalkyl is optionally substituted with             —NR⁶¹R⁶² (wherein R⁶¹ and R⁶² each independently represent             hydrogen or C₁-C₆ alkyl)];     -   wherein R⁷ is         -   hydrogen;         -   halogen;         -   C₁-C₆ alkyl {wherein the C₁-C₆ alkyl is optionally             substituted with hydroxyl, —NR⁷¹R⁷² [wherein R⁷¹ and R⁷²             each independently represent hydrogen, C₁-C₆ alkyl (wherein             the C₁-C₆ alkyl is optionally substituted with             dimethylamino), C₃-C₁₀ cycloalkyl (wherein the C₃-C₁₀             cycloalkyl is optionally substituted with amino), or 3- to             8-membered heterocycloalkyl], or 3- to 8-membered             heterocycloalkyl (wherein the 3- to 8-membered             heterocycloalkyl is optionally substituted with C₁-C₆             aminoalkyl)},         -   C₆-C₁₀ aryl (wherein the C₆-C₁₀ aryl is optionally             substituted with hydroxyl);         -   C₆-C₁₀ arylsulfonyl; or         -   —COR⁷³ {wherein R⁷³ represents 3- to 8-membered             heterocycloalkyl (wherein the 3- to 8-membered             heterocycloalkyl is optionally substituted with amino), or             —NR⁷⁴R⁷⁵ [wherein R⁷⁴ and R⁷⁵ each independently represent             hydrogen, 3- to 8-membered heterocycloalkyl, or C₃-C₁₀             cycloalkyl (wherein the C₃-C₁₀ cycloalkyl is optionally             substituted with amino)]}.

-   2. The compound of above 1, or a pharmaceutically acceptable salt     thereof, wherein

-    is —S—CR⁷═CR⁶—. -   3. The compound of above 2, or a pharmaceutically acceptable salt     thereof, wherein R¹ is hydrogen, cyano, C₁-C₆ alkyl (wherein C₁-C₆     alkyl is optionally substituted with hydroxyl or halogen), C₃-C₁₀     cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, or halogen. -   4. The compound of above 2, or a pharmaceutically acceptable salt     thereof, wherein R² is hydrogen, hydroxyl, halogen, C₁-C₆ alkoxy, or     C₆-C₁₀ aryl which is optionally substituted with hydroxyl. -   5. The compound of above 2 or a pharmaceutically acceptable salt,     wherein R² is hydrogen, hydroxyl, halogen, C₁-C₆ alkoxy, or     dihydroxyphenyl. -   6. The compound of above 2, or a pharmaceutically acceptable salt     thereof, wherein R³ is hydrogen; hydroxyl; C₁-C₆ alkyl (wherein     alkyl is optionally substituted with hydroxyl, halogen, or     hydroxyethylamino); halogen; C₁-C₆ alkoxy optionally substituted     with dimethylamino or morpholinyl; C₁-C₆ alkylphenyl [wherein C₁-C₆     alkyl of the C₁-C₆ alkylphenyl is optionally substituted with     —NR⁵¹R⁵² {wherein R⁵¹ and R⁵² each independently represent hydrogen,     C₁-C₆ alkyl, or —COOR⁵⁶ (wherein R⁵⁶ represents C₁-C₆ alkyl))}];     cyano; nitro; amino; 3- to 8-membered heterocycloalkyl which is     optionally substituted with amino; heteroaryl; —OSO₂CH₃; —OSO₂CF₃;     —OCOR¹⁰³ (R¹⁰³ represents C₁-C₆ alkyl); —OCOOR¹⁰⁴ (wherein R¹⁰⁴     represents C₁-C₆ alkyl); —OCONR¹⁰¹R¹⁰² (wherein R¹⁰¹, R¹⁰² each     independently represent hydrogen or C₁-C₆ alkyl, or R¹⁰¹ and R¹⁰²     together form morpholinyl); or —CONH₂. -   7. The compound of above 2, or a pharmaceutically acceptable salt     thereof, wherein R³ is hydrogen; hydroxyl; C₁-C₆ alkyl (wherein     alkyl is optionally substituted with hydroxyl, halogen, or     hydroxyethylamino); halogen; C₁-C₆ alkoxy that is optionally     substituted with dimethylamino or morpholinyl; C₁-C₆ alkylphenyl     (wherein C₁-C₆ alkyl of the C₁-C₆ alkylphenyl is optionally     substituted with —NR⁵¹R⁵² (wherein R⁵¹ and R⁵² each independently     represent hydrogen, C₁-C₆ alkyl, or —COOR⁵⁶ (wherein R⁵⁶ represents     C₁-C₆ alkyl) cyano; nitro; amino; 3- to 8-membered heterocycloalkyl     which is optionally substituted with amino (wherein the 3- to     8-membered heterocycloalkyl is piperidyl, pyrrolidinyl, morpholinyl,     or piperazinyl); pyridyl; —OSO₂CH₃; —OSO₂CF₃; —OCOR¹⁰³ (R¹⁰³     represents C₁-C₆ alkyl); —OCOOR¹⁰⁴ (wherein R¹⁰⁴ represents C₁-C₆     alkyl); —OCONR¹⁰¹R¹⁰² (wherein R¹⁰¹, R¹⁰² each independently     represent hydrogen or C₁-C₆ alkyl, or R¹⁰¹ and R¹⁰² together form     morpholinyl); or —CONH₂. -   8. The compound of above 2, or a pharmaceutically acceptable salt     thereof, wherein R⁴ is a group selected from the group consisting of     hydrogen, hydroxyl, halogen, amino, C₁-C₆ alkyl, C₂-C₆ alkenyl,     C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₁-C₆ alkoxy, C₆-C₁₀ aryl,     indanyl, heteroaryl, and 3- to 8-membered heterocycloalkyl, wherein     each of the groups of R⁴ is optionally substituted with a     substituent selected from the group consisting of substituent A     above. -   9. The compound of above 2, or a pharmaceutically acceptable salt     thereof, wherein R⁴ is a group selected from the group consisting of     hydrogen, hydroxyl, halogen, amino, C₁-C₆ alkyl, C₂-C₆ alkenyl,     C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₁-C₆ alkoxy, C₆-C₁₀ aryl,     indanyl, heteroaryl (wherein the heteroaryl is selected from the     group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl,     [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl,     2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl,     pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl),     and 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered     heterocycloalkyl is selected from the group consisting of     aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidyl,     piperazinyl, azepanyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl),     wherein each of the groups of R⁴ is optionally substituted with a     substituent selected from the group consisting of substituent A-1     below:     -   substituent A-1:     -   hydroxyl;     -   oxo;     -   cyano;     -   halogen;     -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally substituted         with a substituent selected from the group consisting of         substituent B-1 below);     -   C₃-C₁₀ cycloalkyl [wherein the C₃-C₁₀ cycloalkyl is optionally         substituted with cyano, or C₁-C₆ alkyl substituted with —NR³¹R³²         (wherein R³¹ and R³² each independently represent hydrogen or         C₁-C₆ alkyl)];     -   —NR^(21A)R^(22A) [wherein R^(21A) and R^(22A) each independently         represent hydrogen, C₁-C₆ alkyl (wherein C₁-C₆ alkyl is         optionally substituted with amino, di(C₁-C₆ alkyl)amino, C₁-C₆         alkylsulfonyl (—SO₂ (C₁-C₆ alkyl)), piperidyl, or cyano), or         piperidyl (wherein piperidyl is optionally substituted with         —COOR¹⁰⁵ (wherein R¹⁰⁵ represents C₁-C₆ alkyl))];     -   C₁-C₆ alkoxy {wherein the C₁-C₆ alkoxy is optionally substituted         with 3- to 8-membered heterocycloalkyl selected from halogen,         piperidyl, and piperazinyl (wherein the 3- to 8-membered         heterocycloalkyl is optionally substituted with C₁-C₆ alkyl), or         —NR³³R³⁴ [wherein R³³ and R³⁴ each independently represent         hydrogen, C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally         substituted with C₁-C₆ alkylsulfonyl or di(C₁-C₆ alkyl)amino),         or C₁-C₆ alkylsulfonyl]};     -   —SO₂NR^(23A)R^(24A) (wherein R^(23A) and R^(24A) each         independently represent hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆         alkyl is optionally substituted with hydroxyl, C₁-C₆ alkoxy,         halogen, C₃-C₁₀ cycloalkyl, pyrazolyl, imidazolyl, or —NR³⁵R³⁶         (wherein R³⁵ and R³⁶ each independently represent hydrogen or         C₁-C₆ alkyl)], C₃-C₁₀ cycloalkyl (wherein the C₃-C₁₀ cycloalkyl         is optionally substituted with C₁-C₆ hydroxyalkyl), azetidinyl,         or pyrrolidinyl, or may together form pyrrolidinyl, wherein the         pyrrolidinyl is optionally substituted with amino or halogen);     -   C₁-C₆ alkylsulfonyl (wherein the C₁-C₆ alkyl moiety is         optionally substituted with hydroxyl);     -   C₁-C₆ alkylsulfonylamino (—NHSO₂ (C₁-C₆ alkyl)) [wherein the         C₁-C₆ alkyl moiety is optionally substituted with —NR³⁷R³⁸         (wherein R³⁷ and R³⁸ each independently represent hydrogen or         C₁-C₆ alkyl)];     -   3- to 8-membered heterocycloalkyl selected from the group         consisting of azetidinyl, pyrrolidinyl, piperidyl, piperazinyl,         and tetrahydropyridyl {wherein the 3- to 8-membered         heterocycloalkyl is optionally substituted with —NR³⁹R⁴⁰         (wherein R³⁹ and R⁴⁰ each independently represent hydrogen,         C₁-C₆ alkyl, or C₁-C₆ alkylsulfonyl), C₁-C₆ alkyl [wherein the         C₁-C₆ alkyl is optionally substituted with —NR⁴¹R⁴² (wherein R⁴¹         and R⁴² each independently represent hydrogen or C₁-C₆ alkyl)],         hydroxyl, or C₁-C₆ alkylsulfonyl};     -   1H-tetrazolyl;     -   aryl (wherein aryl is optionally substituted with C₁-C₆ alkyl         [wherein C₁-C₆ alkyl is optionally substituted with cyano or         amino])     -   —COOR¹¹ (wherein R¹¹ represents hydrogen or C₁-C₆ alkyl); and     -   —COR^(12A) [wherein R^(12A) represents piperazinyl which is         optionally substituted with C₁-C₆ alkyl, C₃-C₁₀ cycloalkyl,         cyanomethyl, aminomethyl, —NR²⁵R²⁶ {wherein R²⁵ and R²⁶ each         independently represent hydrogen or C₁-C₆ alkyl [wherein the         C₁-C₆ alkyl is optionally substituted with hydroxyl or —NR⁴³R⁴⁴         (wherein R⁴³ and R⁴⁴ each independently represent hydrogen or         C₁-C₆ alkyl)]}, or C₁-C₆ alkyl];     -   substituent B-1:     -   halogen;     -   hydroxyl;     -   C₁-C₆ alkoxy;     -   cyano;     -   cycloalkyl;     -   phenyl (wherein phenyl is optionally substituted with cyano);     -   heteroaryl selected from the group consisting of imidazolyl,         pyrazolyl, and thiazolyl     -   3- to 8-membered heterocycloalkyl selected from the group         consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl,         and oxetanyl (wherein the 3- to 8-membered heterocycloalkyl is         optionally substituted with C₁-C₆ alkyl, hydroxyl, amino, C₁-C₆         aminoalkyl, or C₁-C₆ alkyl substituted with C₂-C₇         alkyloxycarbonylamino);     -   —NR^(51A)R^(52A) {wherein R^(51A) and R^(52A) each independently         represent hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is         optionally substituted with C₁-C₆ alkylsulfonyl, or piperidyl         which is optionally substituted with, —COOR⁵³ (wherein R⁵³         represents hydro en or C₁-C₆ alkyl)], piperidyl, C₁-C₆         alkylsulfonyl, C₃-C₁₀ cycloalkyl, —COR⁵⁵ (wherein R⁵⁵ represents         C₁-C₆ alkyl), —COOR⁵⁶ (wherein R⁵⁶ represents C₁-C₆ alkyl), or         —CONR⁵⁷R⁵⁸ (wherein R⁵⁷ and R⁵⁸ each independently represent         hydrogen or C₁-C₆ alkyl)};     -   —COOR⁵⁴ (wherein R⁵⁴ represents hydrogen or C₁-C₆ alkyl);     -   —CONH₂;     -   —SO₂NR¹⁰⁶R¹⁰⁷ (wherein R¹⁰⁶ and R¹⁰⁷ each independently         represent hydrogen, C₁-C₆ alkyl, or C₃-C₁₀ cycloalkyl);     -   C₁-C₆ alkylsulfinyl; and     -   C₁-C₆ alkylysulfonyl -   10. The compound of above 9, or a pharmaceutically acceptable salt     thereof, wherein R⁴ is a group selected from the group consisting     of (p) below:     -   (p):         -   hydrogen,         -   hydroxyl,         -   halogen,         -   amino which is optionally substituted with a substituent             selected from the group consisting of substituent (g) below,         -   C₁-C₆ alkyl which is optionally substituted with a             substituent selected from the group consisting of             substituent (a) below,         -   C₂-C₆ alkenyl which is optionally substituted with a             substituent selected from the group consisting of             substituent (b) below,         -   C₃-C₁₀ cycloalkyl,         -   C₃-C₁₀ cycloalkenyl,         -   C₁-C₆ alkoxy,         -   C₆-C₁₀ aryl which is optionally substituted with a             substituent selected from the group consisting of             substituent (c) below,         -   indanyl which is optionally substituted with a substituent             selected from the group consisting of substituent (d) below,         -   heteroaryl which is optionally substituted with a             substituent selected from the group consisting of             substituent (e) below, and         -   3- to 8-membered heterocycloalkyl which is optionally             substituted with a substituent selected from the group             consisting of substituent (f) below,     -   wherein, in the group (p),         -   the heteroaryl is selected from the group consisting of             pyridyl, 1H-indazolyl, 1H-tetrazolyl,             [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl,             2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl,             pyrimidinyl, indolinyl, furyl, thienyl, and             tetrahydroisoquinolyl;         -   the 3- to 8-membered heterocycloalkyl is selected from the             group consisting of pyrrolidinyl, piperidyl, piperazinyl,             morpholinyl, and 1,2,3,6-tetrahydropyridyl;         -   substituent (a):             -   —NR^(21A)R^(22A) [wherein R^(21A) and R^(22A) each                 independently represent hydrogen, C₁-C₆ alkyl {wherein                 C₁-C₆ alkyl is optionally substituted with piperidyl},                 or piperidyl {wherein piperidyl is optionally                 substituted with —COOR¹⁰⁵ (wherein R¹⁰⁵ represents C₁-C₆                 alkyl)}];             -   3- to 8-membered heterocycloalkyl selected from the                 group consisting of pyrrolidinyl and piperidyl {wherein                 the 3- to 8-membered heterocycloalkyl is optionally                 substituted with —NR³⁹R⁴⁰ (wherein R³⁹ and R⁴⁰ each                 independently represent hydrogen or C₁-C₆ alkyl), or                 C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is optionally                 substituted with —NR⁴¹R⁴² (wherein R⁴¹ and R⁴² each                 independently represent hydrogen or C₁-C₆ alkyl)]}; and             -   C₁-C₆ alkylsulfonylamino (—NHSO₂(C₁-C₆ alkyl));         -   substituent (b):             -   —COOR¹¹ (wherein R¹¹ represents hydrogen or C₁-C₆                 alkyl); —NR^(21a)R^(22a) [wherein R^(21a) and R^(22a)                 each independently represent hydrogen, or C₁-C₆ alkyl                 (wherein the C₁-C₆ alkyl is optionally substituted with                 di(C₁-C₆ alkyl)amino or C₁-C₆ alkylsulfonyl)];             -   3- to 8-membered heterocycloalkyl selected from the                 group consisting of azetidinyl, pyrrolidinyl, and                 piperidyl {wherein the 3- to 8-membered heterocycloalkyl                 is optionally substituted with —NR³⁹R⁴⁰ (wherein R³⁹ and                 R⁴⁰ each independently represent hydrogen, C₁-C₆ alkyl,                 or C₁-C₆ alkylsulfonyl), C₁-C₆ alkyl [wherein the C₁-C₆                 alkyl is optionally substituted with —NR⁴¹R⁴² (wherein                 R⁴¹ and R⁴² each independently represent hydrogen or                 C₁-C₆ alkyl)], hydroxyl, or C₁-C₆ alkylsulfonyl};             -   cyano; and             -   C₁-C₆ alkoxy;         -   substituent (c):             -   hydroxyl;             -   cyano;             -   halogen;             -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally                 substituted with a substituent selected from the group                 consisting of substituent B-c below);             -   C₃-C₁₀ cycloalkyl [wherein the C₃-C₁₀ cycloalkyl is                 optionally substituted with cyano, or C₁-C₆ alkyl                 substituted with —NR³¹R³² (wherein R³¹ and R³² each                 independently represent hydrogen or C₁-C₆ alkyl)];             -   —NR^(21c)R^(22c) [wherein R^(21c) and R^(22c) each                 independently represent hydrogen or C₁-C₆ alkyl (wherein                 C₁-C₆ alkyl is optionally substituted with amino, or                 cyano)]];             -   C₁-C₆ alkoxy {wherein the C₁-C₆ alkoxy is optionally                 substituted with 3- to 8-membered heterocycloalkyl                 selected from halogen, piperidyl, and piperazinyl                 (wherein the 3- to 8-membered heterocycloalkyl is                 optionally substituted with C₁-C₆ alkyl), or —NR³³R³⁴                 [wherein R³³ and R³⁴ each independently represent                 hydrogen, C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is                 optionally substituted with di(C₁-C₆ alkyl)amino), or                 C₁-C₆ alkylsulfonyl]};             -   —SO₂NR^(23c)R^(24c) {wherein R^(23c) and R^(24c) each                 independently represent hydrogen, C₁-C₆ alkyl [wherein                 the C₁-C₆ alkyl is optionally substituted with hydroxyl,                 C₁-C₆ alkoxy, halogen, C₃-C₁₀ cycloalkyl, pyrazolyl,                 imidazolyl, or —NR³⁵R³⁶ (wherein R³⁵ and R³⁶ each                 independently represent hydrogen or C₁-C₆ alkyl)],                 C₃-C₁₀cycloalkyl (wherein the C₃-C₁₀ cycloalkyl is                 optionally substituted with C₁-C₆ hydroxyalkyl),                 azetidinyl, or pyrrolidinyl, or wherein R^(23c) and                 R^(24c) may together form pyrrolidinyl which is                 optionally substituted with amino or halogen};             -   C₁-C₆ alkylsulfonyl (wherein the C₁-C₆ alkyl moiety is                 optionally substituted with hydroxyl);             -   C₁-C₆ alkylsulfonylamino (—NHSO₂(C₁-C₆ alkyl)) [wherein                 the C₁-C₆ alkyl moiety is optionally substituted with                 —NR³⁷R³⁸ (wherein R³⁷ and R³⁸ each independently                 represent hydrogen or C₁-C₆ alkyl)];             -   piperazinyl {wherein the piperazinyl is optionally                 substituted with C₁-C₆ alkyl or C₁-C₆ alkylsulfonyl};             -   piperidyl (wherein piperidyl is optionally substituted                 with hydroxyl);             -   1H-tetrazolyl;             -   1,2,3,6-tetrahydropyridyl; and             -   —COR^(12c) [wherein R^(12c) represents piperazinyl which                 is optionally substituted with C₁-C₆ alkyl, C₃-C₁₀                 cycloalkyl, cyanomethyl, aminomethyl, —NR²⁵R²⁶ {wherein                 R²⁵ and R²⁶ each independently represent hydrogen or                 C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is optionally                 substituted with hydroxyl, or —NR⁴³R⁴⁴ (wherein R⁴³ and                 R⁴⁴ each independently represent hydrogen or C₁-C₆                 alkyl)]}, or C₁-C₆ alkyl]; and         -   substituent B-c:             -   halogen;             -   hydroxyl;             -   methoxy;             -   cyano;             -   C₃-C₁₀ cycloalkyl             -   3- to 8-membered heterocycloalkyl selected from the                 group consisting of pyrrolidinyl, piperidyl,                 piperazinyl, morpholinyl, and oxetanyl (wherein the 3-                 to 8-membered heterocycloalkyl is optionally substituted                 with C₁-C₆ alkyl, hydroxyl, amino, C₁-C₆ aminoalkyl, or                 C₁-C₆ alkyl substituted with C₂-C₇                 alkyloxycarbonylamino); and             -   —NR^(51c)R^(52c) {wherein R^(51c) and R^(52c) each                 independently represent hydrogen, C₁-C₆ alkyl [wherein                 the C₁-C₆ alkyl is optionally substituted with C₁-C₆                 alkylsulfonyl, or piperidyl which is optionally                 substituted with —COOR⁵³ (wherein R⁵³ represents                 hydrogen or C₁-C₆ alkyl)], piperidyl,                 C₁-C₆alkylsulfonyl, C₃-C₁₀ cycloalkyl, —COR⁵⁵ (wherein                 R⁵⁵ represents C₁-C₆ alkyl), or —CONR⁵⁷R⁵⁸ (wherein R⁵⁷                 and R⁵⁸ each independently represent hydrogen or C₁-C₆                 alkyl)}];             -   heteroaryl selected from the group of imidazolyl,                 pyrazolyl, and thiazolyl;             -   —COOR⁵⁴ (wherein R⁵⁴ represents hydrogen, or C₁-C₆                 alkyl)             -   —CONH₂;             -   —SO₂NR¹⁰⁶R¹⁰⁷ wherein R¹⁰⁶ and R¹⁰⁷ each independently                 represent hydrogen, C₁-C₆ alkyl, or C₃-C₁₀ cycloalkyl);             -   C₁-C₆ alkylsufinyl; and             -   C₁-C₆ alkylsulfonyl;         -   substituent (d):             -   —NR^(21d)R^(22d) (wherein R^(21d) and R^(22d) each                 independently represent hydrogen or C₁-C₆ alkyl);         -   substituent (e):             -   hydroxyl;             -   oxo;             -   cyano;             -   C₃-C₁₀ cycloalkyl [wherein C₃-C₁₀ cycloalkyl is                 optionally substituted with cyano];             -   —NR²¹R²² [wherein R²¹ and R²² each independently                 represent hydrogen or C₁-C₆ alkyl (wherein C₁-C₆ alkyl                 is optionally substituted with amino)];             -   piperidyl;             -   C₁-C₆ alkoxy (wherein C₁-C₆ alkoxy is optionally                 substituted with —NR³³R³⁴ [wherein R³³ and R³⁴ each                 independently represent hydrogen, or C₁-C₆ alkyl]); and             -   C₁-C₆ alkyl {wherein the C₁-C₆ alkyl is optionally                 substituted with cyano, —NR^(51e)R^(52e) [wherein                 R^(51e) and R^(52e) each independently represent                 hydrogen, C₁-C₆ alkyl, or —COOR⁵⁶ (wherein R⁵⁶                 represents C₁-C₆ alkyl)], morpholinyl, or cyanophenyl};                 —CONH₂;         -   substituent (f):             -   C₁-C₆ alkyl {wherein the C₁-C₆ alkyl is optionally                 substituted with —NR^(51f)R^(52f) [wherein R^(51f) and                 R^(52f) each independently represent hydrogen, C₁-C₆                 alkyl, or —COOR⁵⁶ (wherein R⁵⁶ represents C₁-C₆                 alkyl)]}; and C₁-C₆ alkylsulfonyl;         -   substituent (g):         -   Aryl (wherein aryl is optionally substituted with C₁-C₆             alkyl [wherein C₁-C₆ alkyl is optionally substituted with             cyano or amino]). -   11. The compound of above 2, or a pharmaceutically acceptable salt     thereof, wherein R⁶ is hydrogen; hydroxyl; C₁-C₆ alkyl; phenyl which     is optionally substituted with 1 to 3 hydroxyls; piperidyl which is     optionally substituted with amino; or piperazinyl. -   12. The compound of above 11, or a pharmaceutically acceptable salt     thereof, wherein R⁷ is hydrogen, C₁-C₆ alkyl (wherein C₁-C₆ alkyl is     optionally substituted by a substituent selected from the group     comprising hydroxyl and piperidyl), or halogen. -   13. The compound of above 2, or a pharmaceutically acceptable salt     thereof, wherein R⁷ is hydrogen;     -   C₁-C₆ alkyl {wherein the C₁-C₆ alkyl is optionally substituted         with hydroxyl, —NR^(71A)R^(72A) [wherein R^(71A) and R^(72A)         each independently represent hydrogen, C₁-C₆ alkyl (wherein the         C₁-C₆ alkyl is optionally substituted with dimethylamino),         C₃-C₁₀ cycloalkyl (wherein the C₃-C₁₀ cycloalkyl is optionally         substituted with amino), or piperidyl], or 3- to 8-membered         heterocycloalkyl selected from the group consisting of piperidyl         and morpholinyl (wherein the 3- to 8-membered heterocycloalkyl         is optionally substituted with C₁-C₆ aminoalkyl)};     -   phenyl which is optionally substituted with 1 to 2 hydroxyls;     -   phenylsulfonyl; or     -   —COR^(73A) {wherein R^(73A) represents piperidyl (wherein the         piperidyl is optionally substituted with amino), or         —NR^(74A)R^(75A) [wherein R^(74A) and R^(75A) each independently         represent hydrogen, piperidyl, or C₃-C₁₀ cycloalkyl (wherein the         C₃-C₁₀ cycloalkyl is optionally substituted with amino)]}. -   14. The compound of above 1, or a pharmaceutically acceptable salt     thereof, wherein

-    is —CH₂—CH₂—CH₂—. -   15. The compound of above 14, or a pharmaceutically acceptable salt     thereof, wherein R¹ and R² are hydrogen. -   16. The compound of above 14, or a pharmaceutically acceptable salt     thereof, wherein R³ is hydroxyl or methoxy. -   17. The compound of above 14, or a pharmaceutically acceptable salt     thereof, wherein R⁴ is hydrogen, phenyl [wherein the phenyl is     substituted with C₁-C₆ alkyl substituted with —NR^(51A)R^(52A)     (wherein R^(51A) and R^(52A) each independently represent hydrogen     or C₁-C₆ alkyl), or —SO₂NR^(53A)R^(54A)(wherein R^(53A) and R^(54A)     each independently represent hydrogen, or C₁-C₆ alkyl that is     optionally substituted with halogen or hydroxyl)],     1,2,3,6-tetrahydropyridyl, hydroxypyridyl, or methoxypyridyl. -   18. The compound of above 1, or a pharmaceutically acceptable salt     thereof, wherein

-    is —NR¹⁰⁸—CH═CR¹⁰⁹— (wherein R¹⁰⁸ represents hydrogen, or C₁-C₆     alkyl that is optionally substituted with hydroxyl, and R¹⁰⁹     represents hydrogen, CH₃, or phenyl group which is substituted with     C₁-C₆-aminoalkyl),     -   R¹, R², and R⁴ are hydrogen, and     -   R³ is hydrogen, hydroxyl or C₁-C₆alkoxy. -   19. The compound of above 1, or a pharmaceutically acceptable salt     thereof, wherein

-    is —N═CH—S—,     -   R¹, R², and R⁴ are hydrogen, and     -   R³ is methoxy. -   20. A compound selected from the group consisting of: -   (1): 8-methoxy-5-methylthieno[2,3-c]quinolin-4(5H)-one; -   (2): 8-hydroxy-5-methylthieno[2,3-c]quinolin-4(5H)-one; -   (3): 7,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one; -   (4): 7,8-dimethoxythieno[2,3-c]quinolin-4(5H)-one; -   (5): 8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (6): 7,9-dimethoxythieno[2,3-c]quinolin-4(5H)-one; -   (7): 7,9-dihydroxythieno[2,3-c]quinolin-4(5H)-one; -   (8): 7,8,9-trimethoxythieno[2,3-c]quinolin-4(5H)-one; -   (9): 8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (10): 7,8,9-trihydroxythieno[2,3-c]quinolin-4(5H)-one; -   (11):     9-(3-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (12): 8-chlorothieno[2,3-c]quinolin-4(5H)-one; -   (13): 4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; -   (14): thieno[2,3-c]quinolin-4(5H)-one; -   (15): 8-fluorothieno[2,3-c]quinolin-4(5H)-one; -   (16): 8-nitrothieno[2,3-c]quinolin-4(5H)-one; -   (17): 8-(3-aminopiperidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (18): 1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (19): 1,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one; -   (20): 8-hydroxy-1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (2H): (R)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (22): (S)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (23): 8-(pyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (24): 8-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (25):     1-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (26):     1-(3-aminopiperidin-1-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (27): 8-morpholinothieno[2,3-c]quinolin-4(5H)-one; -   (28): 8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one; -   (29): 8-hydroxy-2-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (30):     8-hydroxy-4-oxo-N-(piperidin-3-yl)-4,5-dihydrothieno[2,3-c]quinoline-2-carboxamide; -   (31): 8-hydroxy-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (32): 8-hydroxy-1-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (33):     N-((1r,4r)-4-aminocyclohexyl)-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-2-carboxamide; -   (34):     2-(3-aminopiperidine-1-carbonyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (35):     2-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (36):     2-(((1r,4r)-4-aminocyclohexylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (37): 8-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (38): 8-hydroxy-1-methylthieno[2,3-c]quinolin-4(5H)-one; -   (39):     2-((2-(dimethylamino)ethylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one; -   (40):     8-hydroxy-2-((piperidin-3-ylamino)methyl)thieno[2,3-c]quinolin-4(5H)-one; -   (41): 7-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (42): 9-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (43):     9-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (44):     1-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; -   (45):     7-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (46): 8-hydroxy-1-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one; -   (47):     9-(3,5-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (48): 8-hydroxy-9-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (49): 8-hydroxy-9-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (50):     9-(3,4-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (51):     (S)-8-(3-aminopyrrolidin-1-yl)-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (52):     5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)picolinonitrile; -   (53):     9-(6-aminopyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (54):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (55):     9-(3-fluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (56): 8-hydroxy-2-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (57):     (R)-8-(3-aminopyrrolidin-1-yl)-2-(3,4-dihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (58):     9-(3,4-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (59):     9-(4-fluoro-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (60):     8-hydroxy-9-(3-hydroxy-5-(trifluoromethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (61): 8-hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (62):     8-hydroxy-9-(3,4,5-trihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (63): 9-(4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (64):     9-(4-(1H-tetrazol-5-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (65):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (66):     9-(3-chloro-4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (67):     9-(4-chloro-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (68):     9-(3,4-dichlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (69): 9-(4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (70): 8-hydroxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one; -   (71):     9-(4-(difluoromethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (72):     9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (73):     9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (74): 9-(3-aminophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (75):     3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (76):     8-hydroxy-9-(3,4,5-trifluorophenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (77):     N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (78): 8-methoxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one; -   (79): 8-hydroxy-9-(naphthalen-2-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (80):     8-hydroxy-9-(4-(hydroxymethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (81):     2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (82):     8-hydroxy-9-(4-(methylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (83): 8-hydroxy-9-(pyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (84):     8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (85):     8-hydroxy-9-(4-hydroxy-3-methoxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (86):     9-(3-fluoro-4-(morpholinomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (87):     9-(3-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (88):     9-(4-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (89):     9-(3-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (90):     9-(3-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one; -   (91): 9-cyclohexenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (92):     9-(3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (93):     9-(4-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (94):     9-(3-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (95):     9-(4-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one; -   (96): 9-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (97):     9-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (98):     8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (99): 9-cyclohexenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (100):     8-methoxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (101):     9-(4-(aminomethyl)phenyl)-8-hydroxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (102):     9-(1H-benzo[d]imidazol-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (103):     9-(4-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (104):     9-(4-(aminomethyl)phenyl)-8-methoxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (105):     8-hydroxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (106):     8-hydroxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (107): 8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (108): 8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (109):     5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzo[d]oxazol-2(3H)-one; -   (110): tert-butyl     4-(2-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylamino)ethyl)piperidine-1-carboxylate; -   (111):     8-methoxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (112):     8-hydroxy-9-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (113):     8-hydroxy-9-(4-((piperidin-3-ylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (114):     N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (115):     9-(4-(3-(dimethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one; -   (116):     8-methoxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (117):     8-hydroxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (118): 8-methoxythiazolo[4,5-c]quinolin-4(5H)-one; -   (119):     2-((4-(aminomethyl)piperidin-1-yl)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (120):     N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (121):     9-(4-(aminomethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (122): (E)-butyl     3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)acrylate; -   (123):     8-methoxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (124):     8-hydroxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (125):     N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide; -   (126):     N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (127):     N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (128):     N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide; -   (129): 4-(8-hydroxy-4     oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide; -   (130):     8-hydroxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (131):     8-methoxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (132):     8-hydroxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (133):     8-methoxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (134):     (E)-9-(3-(diethylamino)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (135):     (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (136):     (E)-9-(3-(2-(diethylamino)ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (137):     N-(4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)phenyl)methanesulfonamide; -   (138):     9-(2-(dimethylamino)pyrimidin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (139):     tert-butyl(1-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)piperidin-4-yl)methylcarbamate; -   (140):     8-hydroxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (141):     8-methoxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (142):     8-methoxy-9-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (143):     (E)-9-(3-(diethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (144):     9-(3-(4-(aminomethyl)piperidin-1-yl)propyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (145):     9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one; -   (146):     9-(4-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (147):     9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one; -   (148):     (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (149):     9-(4-(3-(dimethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (150):     8-hydroxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (151):     9-(4-(2-(ethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (152):     (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (153):     9-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (154):     9-(4-(2-(ethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (155):     9-(4-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (156):     9-(4-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (157):     9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (158):     9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (159):     8-methoxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (160):     8-methoxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (161):     9-(3-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (162):     9-(3-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (163):     9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (164):     9-(4-((dimethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (165):     9-(4-((dimethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (166):     9-(3-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (167):     8-hydroxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (168):     N-ethyl-N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylmethoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenoxy)ethyl)methanesulfonamide; -   (169):     9-(4-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (170):     2-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (171):     2-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (172):     9-(1-(2-(dimethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (173):     N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (174):     9-(1-(2-(diethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (175):     9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (176):     9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (177):     N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (178):     N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (179):     N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide; -   (180):     8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (181):     9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (182):     9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (183):     9-(4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (184):     9-(4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (185):     9-(3-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (186):     9-(3-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (187):     8-hydroxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (188):     8-methoxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (189):     9-(4-amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (190): 3-(8-hydroxy-4     oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile; -   (191):     9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (192):     9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (193):     N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide; -   (194):     8-hydroxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (195):     9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (196):     9-(4-(1-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (197):     N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide; -   (198):     N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (199):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(pyrrolidin-3-yl)benzenesulfonamide; -   (200):     N-(azetidin-3-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide; -   (201):     9-(4-(2-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (202):     2-amino-N-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; -   (203):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile; -   (204):     4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile; -   (205):     (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (206):     N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (207):     8-methoxy-9-(5-methoxypyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (208):     8-methoxy-9-(5-methoxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (209):     9-(4-(3-aminopyrrolidin-1-ylsulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (210):     N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide; -   (211):     9-(4-((diisopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (212):     N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)methanesulfonamide; -   (213):     9-(4-((isopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (214):     2-(dimethylamino)-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; -   (215):     2-amino-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; -   (216):     8-methoxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (217):     9-(4-amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (218):     N-(2-methoxy-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (219):     9-(3,5-difluoro-4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (220):     N-(2-hydroxy-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (221):     9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (222):     9-(4-(2-(dimethylamino)ethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (223):     9-(3,5-difluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (224):     6-fluoro-8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (225):     9-(4-(1-(dimethylamino)ethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-(5H)-one; -   (226):     9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (227):     (E)-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (228):     (E)-8-hydroxy-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one -   (229):     8-hydroxy-9-(4-((isopropylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (230):     (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (231):     (E)-8-methoxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one; -   (232):     (S)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (233):     (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (234):     8-hydroxy-9-(5-hydroxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (235):     9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (236):     8-methoxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (237):     9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (238):     (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (239):     (E)-9-(3-(ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (240):     9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (241):     9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (242):     9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (243):     8-hydroxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (244):     (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (245):     (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (246):     (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (247):     (E)-8-hydroxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one; -   (248):     8-methoxy-9-(4-(2-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-(5H)-one; -   (249):     2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (250):     (E)-N-(1-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl)azetidin-3-yl)methanesulfonamide; -   (251):     4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide; -   (252):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide; -   (253): tert-butyl     (5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)furan-2-yl)methylcarbamate; -   (254):     N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide; -   (255):     N-(4-(8-methoxy-1-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide; -   (256):     9-(4-(aminomethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (257):     9-(4-(aminomethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (258):     6-fluoro-8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (259):     9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (260):     8-methoxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (261):     2-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (262):     8-hydroxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (263):     (E)-9-(3-(3-(dimethylamino)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (264):     (E)-9-(3-(3-(dimethylamino)pyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (265):     9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (266):     9-(5-(aminomethyl)thiophen-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (267):     9-(4-((ethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (268):     (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (269):     9-(4-((ethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (270):     9-(4-(aminomethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (271):     9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (272):     (R)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (273):     9-(4-(3-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (274):     (R)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (275):     (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (276):     9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (277):     9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (278):     9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (279):     9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (280):     4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide; -   (281):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide; -   (282):     N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (283):     8-hydroxy-9-(4-((2-(methylsulfonyl)ethylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (284):     9-(3-(3-(dimethylamino)pyrrolidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (285):     9-(1-(2-aminoethyl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (286):     9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (287):     4-(7-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; -   (288): 9-(3-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (289):     2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide; -   (290):     3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (291): 9-(4-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (292):     2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (293):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide; -   (294):     1,1-diethyl-3-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)urea; -   (295):     N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (296): 9-(4-acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (297):     N-(2-bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (298):     9-(3-(3-(dimethylamino)piperidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (299):     N-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (300):     9-(3-fluoro-4-(2-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     methanesulfonate; -   (301):     (R)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide; -   (302):     (R)-9-(4-(1-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     methanesulfonate; -   (303):     2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (304):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide; -   (305):     9-(4-(2-(dimethylamino)ethyl)phenyl)-7-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (306):     N-(2-bromoethyl)-4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (307):     4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; -   (308):     9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (309):     N-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)-N-methyl     methanesulfonamide; -   (310): 4-(8-hydroxy-4     oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide; -   (311):     (E)-3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylacrylonitrile; -   (312):     N-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (313):     8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (314):     9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (315):     9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (316):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; -   (317):     9-(5-(aminomethyl)furan-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (318):     9-(3-chloro-4-((methylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (319):     9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (320):     N-(3-hydroxypropyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (321):     2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; -   (322):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3-hydroxypropyl)benzensulfonamide; -   (323):     N-(3-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (324):     2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide; -   (325):     9-(3-chloro-4-((methylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (326): 9-(4-(aminomethyl)phenyl)-4     oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; -   (327):     9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one; -   (328):     9-(4-(aminomethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (329):     9-(4-(aminomethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (330):     9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     trifluoromethanesulfonate; -   (331):     9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (332):     N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (333):     N-(2-fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (334):     9-(4-(2-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (335):     (S)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (336):     9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (337):     9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (338):     9-(4-(1-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (339):     9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (340): 9-amino-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (341):     9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (342):     9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (343):     N-cyclopropyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (344):     N-cyclopropyl-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (345):     9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (346):     9-(4-(1-(dimethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (347):     (S)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide; -   (348):     9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (349):     9-(4-(1-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (350):     N-(1-(hydroxymethyl)cyclopentyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (351):     9-(2-(diethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (352):     9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (353):     8-hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (354):     8-methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (355):     3-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (356):     9-(4-(1-(diethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (357):     1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile; -   (358):     9-(2-ethyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (359):     9-(4-(1-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (360):     3-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (361):     1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile; -   (362):     9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (363):     N-isopentyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (364):     9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (365):     9-(4-(1-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (366):     6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (367):     9-(4-(cyclopropanecarbonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (368):     9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carboxamide; -   (369): 9-(2-aminoethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (370):     8-hydroxy-9-(4-(2-hydroxyethylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (371):     9-(4-(2-hydroxyethylsulfonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (372):     9-(1-ethylindolin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (373):     9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (374):     8-hydroxy-9-(2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (375):     9-(4-(1-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (376):     8-hydroxy-9-(1-methylindolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (377): 8-hydroxy-9-(indolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (378): 9-(indolin-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (379):     9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (380):     4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-propylbenzenesulfonamide; -   (381):     N-(cyclopropylmethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (382):     N-(3,3-dimethylbutyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (383):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-isopentylbenzenesulfonamide; -   (384):     N-(3,3-dimethylbutyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (385):     9-(4-(1-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (386):     3-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-oxopropanenitrile; -   (387):     (E)-9-(2-ethoxyvinyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (388):     N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)acetamide; -   (389):     4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide; -   (390):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(1-(hydroxymethyl)cyclopentyl)benzenesulfonamide; -   (391):     N-(2,2-difluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1031):     8-methoxy-9-(4-(1-methoxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1032):     9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1033):     8-methoxy-9-(2-((piperidin-3-ylmethyl)amino)ethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1034):     9-(2-(4-((dimethylamino)methyl)piperidin-1-yl)ethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1035): tert-butyl     4-((2-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)ethyl)amino)piperidine-1-carboxylate; -   (1036):     8-methoxy-9-(2-(piperidin-4-ylamino)ethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1037):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide; -   (1038): 3H-pyrrolo[2,3-c]quinolin-4(5H)-one; -   (1039):     9-(4-(1-aminoethyl)phenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1040):     9-(4-(1-aminoethyl)phenyl)-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-6-carbonitrile; -   (1041):     9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1042):     8-hydroxy-9-(2-(4-((methylamino)methyl)piperidin-1-yl)ethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1043):     8-methoxy-9-(2-(4-((methylamino)methyl)piperidin-1-yl)ethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1044):     9-(2-(4-((dimethylamino)methyl)piperidin-1-yl)ethyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1045):     9-(4-(1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1046):     (R)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1047):     (R)-8-(4-(1-aminoethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1048): (R)-tert-butyl     (1-(4-(4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl)phenyl)ethyl)carbamate; -   (1049):     9-(4-(4-hydroxypiperidin-4-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1050):     (R)-8-(4-(1-(dimethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1051):     8-hydroxy-9-(4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1052):     (R)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1053):     8-hydroxy-9-(4-(1-hydroxypropyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1054):     (R)-8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1055):     8-hydroxy-9-(4-(4-hydroxypiperidin-4-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1056):     (S)-8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1057):     N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1058):     9-(4-(hydroxy(thiazol-2-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1059):     9-(6-(1-aminoethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1060):     9-(4-(4-hydroxybutyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1061):     2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropanamide; -   (1062):     N-(1-bromopropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1063):     8-hydroxy-9-(4-(hydroxy(thiazol-2-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1064):     (S)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1065):     9-(6-(1-(diethylamino)ethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1066):     9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1067):     9-(6-(1-aminoethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1068):     8-hydroxy-9-(4-(4-hydroxybutyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1069):     9-(4-(3-amino-1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1070):     9-(6-(1-(dimethylamino)ethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1071):     9-(6-(1-(dimethylamino)ethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1072):     4-((4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-1H-pyrazol-1-yl)methyl)benzonitrile; -   (1073): 8-aminothieno[2,3-c]quinolin-4(5H)-one; -   (1074):     9-(4-((1H-pyrazol-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1075):     9-(6-(1-aminoethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1076):     9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     dimethylcarbamate; -   (1077):     9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     isopropyl carbonate; -   (1078):     9-(4-((1H-imidazol-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1079):     N-(2-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1080):     (R)-9-(4-(1-aminoethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1081):     (R)-9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1082):     (S)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1083):     9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     diethylcarbamate; -   (1084):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide; -   (1085):     N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide; -   (1086):     9-(4-((1H-pyrazol-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1087):     (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1088):     9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1089):     9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     morpholine-4-carboxylate; -   (1090):     N-(2-hydroxyethyl)-4(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide; -   (1091): 8-bromothieno[2,3-c]quinolin-4(5H)-one; -   (1092):     9-(4-(2-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1093):     9-(4-(2-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1094): N-(2-bromoethyl)-4-(8-hydroxy-4     oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide; -   (1095):     9-(4-(2-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1096):     8-methoxy-9-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (1097):     9-(4-(2-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1098):     9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1099):     9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     acetate; -   (1100):     9-(1-(1-(dimethylamino)propan-2-yl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1101):     9-(4-((1H-imidazol-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1102):     9-(4-(aminomethyl)phenyl)-8-(2-morpholinoethoxy)thieno[2,3-c]quinolin-4(5H)-one; -   (1103):     8-hydroxy-9-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (1104):     N-(2-(1H-pyrazol-1-yl)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1105):     8-hydroxy-9-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1106):     9-(4-(2-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1107):     N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropyl)methanesulfonamide; -   (1108):     9-(4-(2-(dimethylamino)propyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1109): 9-(4-(1-aminoethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1110):     9-(1-(1-(dimethylamino)propan-2-yl)-1H-pyrazol-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1111):     9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1112):     9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1113):     8-methoxy-9-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1114):     N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide; -   (1115):     N-(2-(1H-imidazol-1-yl)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1116):     9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1117):     3-(4-(8-(2-(dimethylamino)ethoxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (1118):     (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1119):     N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide; -   (1120):     (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1121):     (S)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1122):     (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1123):     (R)-9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1124):     9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; -   (1125):     9-(4-(1-aminoethyl)phenyl)-8-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1126):     (R)-6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1127):     (S)-9-(4-(1-(ethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1128):     (S)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1129):     6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1130):     9-(4-(1-aminoethyl)phenyl)-6-ethynyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1131):     (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1132):     (R)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1133):     9-(4-(2-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-(5H)-one; -   (1134):     9-(4-(1-aminoethyl)phenyl)-8-(difluoromethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1135):     (R)-6-bromo-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1136):     9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1137): 9-(4-butylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1138): 9-(4-butylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1139):     N-(2-chloroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1140):     9-(4-((3-bromopyrrolidin-1-yl)sulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1141):     (S)-9-(4-(1-(methylsulfonamido)propyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     methanesulfonate; -   (1142):     9-(4-(2-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1143):     9-(4-(3-(dimethylamino)-1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1144):     N-(2-bromoethyl)-4-(6-chloro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1145):     N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide; -   (1146):     N-(2-bromoethyl)-4-(5-ethyl-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1147):     (S)-8-methoxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1148):     (S)-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1149):     9-(4-(1-aminoethyl)phenyl)-8-(((2-hydroxyethyl)amino)methyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1150):     (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1151):     (R)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1152): 8-hydroxy-9-(4-pentylphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1153):     9-(4-(2-aminoacetyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1154):     (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1155):     8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1156):     8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1157):     (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1158):     (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1159):     (R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1160):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1161):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1162):     2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butanenitrile; -   (1163):     (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1164):     (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1165):     6-chloro-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1166):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1167):     9-(4-(2-aminoethyl)-3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1168):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one -   (1169):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one -   (1170):     6-chloro-8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1171):     9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1172):     (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1173):     6-bromo-8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1174):     9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1175):     (R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1176):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1177):     9-(4-(2-aminoethyl)-3,5-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1178):     9-(4-(2-(dimethylamino)ethyl)-3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1179):     9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1180):     (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6,7-dichloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1181):     (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1182):     (S)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1183):     6-bromo-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1185):     N-(2-hydroxyethyl)-4-(8-methoxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1186): methyl     3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanoate; -   (1187):     (R)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1188):     (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1189):     (R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1190):     9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1191):     9-(4-(2-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1192):     9-(4-(2-aminoethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1193):     9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1194):     (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1195):     (S)-6-chloro-9-(4-(1-(diethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1196):     (S)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1197):     (S)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1198):     4-(8-hydroxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; -   (1199):     N-(2-bromoethyl)-4-(8-hydroxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1200):     (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1201):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1202):     9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1203):     9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-2-(phenylsulfonyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1204):     N-(1-chloropropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1205):     N-(1-chloropropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (1206):     9-(4-(2-aminoethyl)-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1207):     9-(4-(2-aminoethyl)-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1208):     9-(4-(2-aminoethyl)-2-chloro-5-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1209):     9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1210):     (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-5,6-dimethylthieno[2,3-c]quinolin-4(5H)-one; -   (1211):     9-(4-(2-aminoethyl)-2-chloro-5-hydroxyphenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1212):     9-(4-(aminomethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1213):     9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1214):     9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1215):     (S)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1216):     9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1217):     9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1218):     9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-(5H)-one; -   (1219):     9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1220):     9-(4-(2-aminoethyl)-3-fluorophenyl)-6-cyclopropyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1221):     9-(4-(2-aminoethyl)-3-fluorophenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1222):     (S)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1223):     (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1224):     9-(4-(2-aminoethyl)-2-bromo-5-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1225):     (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1226):     3-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (1227):     9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1228):     9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1229):     2-(2-fluoro-4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (1230):     6-cyclopropyl-9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1231):     6-cyclopropyl-9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1232):     (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1233):     (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1234):     9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1235):     9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1236):     9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1237):     9-(4-(2-amino-1,1-dicyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1238):     3-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (1239):     9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1240):     9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1241):     9-(4-(3-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1242):     9-(4-(2-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1243):     9-(4-(2-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1244):     9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-cyclopropyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1245):     6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1246):     6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1247):     9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1248):     9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1249):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-carbonitrile; -   (1250):     (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-vinylthieno[2,3-c]quinolin-4(5H)-one; -   (1251):     9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1252):     9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1253):     9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1254):     9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1255):     (R)-9-(4-(1-aminoethyl)phenyl)-6-ethyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1256):     (R)-9-(4-(1-aminoethyl)phenyl)-6-(difluoromethyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1257):     9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1258):     9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1259):     6-bromo-9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1260):     9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1261):     9-(4-(3-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1262):     (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1263):     9-(4-(2-aminoethyl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1264):     9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1265):     (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1266):     9-(4-(2-aminopropyl)phenyl)-6-ethyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1267):     (R)-9-(4-(1-aminoethyl)phenyl)-6-butyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1268):     9-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-(5H)-one; -   (1269):     9-(4-(2-aminopropyl)phenyl)-6-ethyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1270):     2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-(oxetan-3-yl)acetonitrile; -   (1271):     9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1272):     (R)-6-ethyl-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1273):     9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1274):     9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1275):     9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1276):     9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1277):     9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1278):     9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1279):     9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1280):     9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1281):     9-(4-(2-amino-2-methylpropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1282):     9-(4-(2-amino-2-methylpropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1283):     9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1284):     8-methoxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1285):     8-hydroxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1286):     9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1287):     9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1288):     9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1289):     9-(4-(2-amino-2-methylpropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1290):     9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1291):     9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1292):     9-(4-(2-amino-2-methylpropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1293):     9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1294):     9-(3-fluoro-4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1295):     9-(4-(1-(dimethylamino)-3-methylbutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1296):     9-(4-(1-(dimethylamino)-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1297):     9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1298):     (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1299):     9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1300):     9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1301):     8-methoxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1302):     8-hydroxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1303):     (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1304):     (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1305):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1306):     (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1307):     (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1308): 8-methoxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one; -   (1309):     9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1310):     (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1311):     (R)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1312):     9-(4-(1-aminobutan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1313): 8-hydroxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one; -   (1314): 9-amino-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1315):     (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1316):     (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1317):     (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1318):     (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1319):     (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1320):     9-((4-(2-aminoethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1321):     9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-(5H)-one; -   (1322):     (R)-1-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one; -   (1323):     8-hydroxy-3-(hydroxymethyl)-3H-pyrrolo[2,3-c]quinolin-4(5H)-one; -   (1324):     (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1325):     9-((4-(aminomethyl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1326):     9-((4-(aminomethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1327):     9-((4-(1-aminopropan-2-yl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1328):     9-((4-(1-aminopropan-2-yl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1329):     9-(4-(2-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1330):     9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1331):     9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1332):     9-(4-((R)-1-aminopropan-2-yl)phenyl)-8-hydroxy-2-(1-hydroxyethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1333):     9-(4-((R)-1-aminopropan-2-yl)phenyl)-2-(1-hydroxyethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1334):     3-(4-((8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)amino)phenyl)propanenitrile; -   (1335):     9-((3-(2-aminoethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1336):     9-((4-(2-aminoethyl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1337):     9-(4-(2-(ethylamino)propyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1338):     9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one; -   (1339):     9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1340):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one; -   (1341):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one; -   (1342):     9-(4-((R)-1-aminopropan-2-yl)phenyl)-2-(1-hydroxyethyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1343):     2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)amino)acetonitrile; -   (1344):     (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1345):     9-(3-chloro-4-(2-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1346):     9-(4-(3-((dimethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1347):     (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1348):     9-(4-(2-(ethylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1349):     9-(4-(2-(ethylamino)ethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1350):     9-(4-(2-(ethyl(methyl)amino)propyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1351):     2-(hydroxy(piperidin-4-yl)methyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1352):     (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1353):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1354):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1355):     8-methoxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1356):     9-(4-(2-(ethyl(methyl)amino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1357):     9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1358):     9-(4-(3-((dimethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1359):     9-(6-(dimethylamino)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1360):     (R)-9-(4-(1-(dimethylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1361):     (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1362):     9-(4-(3-((diethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1363):     9-(3-chloro-4-(2-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1364):     8-hydroxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1365):     (R)-9-(4-(1-(dimethylamino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1366):     (R)-9-(4-(1-(ethyl(methyl)amino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1367):     (R)-9-(4-(1-(diethylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1368):     (R)-9-(4-(1-(ethyl(methyl)amino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1369):     2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino)acetonitrile; -   (1370):     2-((4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino)acetonitrile; -   (1371):     9-(3-chloro-4-(2-(ethyl(methyl)amino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1372):     9-(4-(1-((dimethylamino)methyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1373):     (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1374):     9-(6-(2-aminoethoxy)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1375):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1376):     9-(6-(2-aminoethoxy)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1377):     9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1378):     9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1379):     (R)-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1380):     (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1381):     9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1382):     (R)-1-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-3-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one; -   (1383):     (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1384):     9-(6-((2-aminoethyl)amino)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1385):     9-(6-((2-aminoethyl)amino)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1386):     (S)-6-chloro-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1387):     (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1388):     (R)-9-(4-(1-(diethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1389):     9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1390):     9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1391):     9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1392):     (4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (1393):     8-methoxy-6-methyl-9-(4-(2-(methylsulfinyl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1394):     8-hydroxy-6-methyl-9-(4-((methylsulfonyl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1395):     (4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (1396):     9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1397):     (R)—N-(2-(2-fluoro-4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; -   (1398):     (R)—N-(2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; -   (1399):     (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1400):     9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1401):     9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1402):     2-(6-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-3-yl)acetonitrile; -   (1403):     8-hydroxy-6-methyl-9-(4-(2-(methylsulfinyl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1404):     8-methoxy-6-methyl-9-(4-((methylsulfonyl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (1405):     5-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)nicotinamide; -   (1406):     2-(5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)propanenitrile; -   (1407):     2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanamide; -   (1408):     9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1409):     2-(5-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile; -   (1410):     2-hydroxy-2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide; -   (1411):     N-(tert-butyl)-2-hydroxy-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide; -   (1412):     2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanamide; -   (1413):     2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide; -   (1414):     9-(4-(2-amino-1-fluoroethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1415):     9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1416):     2-(5-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile; -   (1417):     2-(5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile; -   (1418):     2-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile; -   (1419):     2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide; -   (1420):     9-(4-(2-amino-1-hydroxyethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; -   (1421):     9-(6-(1-amino-2-methylpropan-2-yl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (1422):     N-cyclopropyl-1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (1423):     2-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)propanenitrile; -   (1424):     (R)—N-(2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; -   (1425):     N-ethyl-1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (1426):     9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (1427):     N-cyclopropyl-1-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (1428):     1-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)cyclopropanecarbonitrile; -   (1429):     N-ethyl-1-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (1430):     1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; -   (1431):     1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; -   (1432):     (R)—N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; -   (1433):     (R)—N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide; -   (1434):     (R)—N-(2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; -   (1435):     (R)—N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; -   (1436):     (R)—N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide; -   (1437):     (R)—N-(2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide; -   (1438):     (R)—N-(2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide;     -   or a pharmaceutically acceptable salt thereof. -   21. A pharmaceutical composition comprising at least one compound of     above 1 or 2 or a pharmaceutically acceptable salt thereof, and a     pharmaceutically acceptable carrier. -   22. The pharmaceutical composition of above 21 which is available     for preventing or treating a PBK dependent disease. -   23. The pharmaceutical composition of above 22, wherein the PBK     dependent disease is cancer. -   24. A PBK inhibitor comprising at least one compound of above 1 or     2, or a pharmaceutically acceptable salt thereof. -   25. A method for treating a PBK dependent disease in a subject,     comprising administering to said subject an effective amount of a     compound or a pharmaceutically acceptable salt thereof of above 1 or     2. -   26. A compound or pharmaceutically acceptable salt thereof of above     1 or 2 for use in treatment of a PBK dependent disease. -   27. Use of a compound of above 1 or 2 or a pharmaceutically     acceptable salt thereof in manufacturing a pharmaceutical     composition for treating a PBK dependent disease.

Alternatively, the present invention also provides following embodiments:

-   101. The present invention provides a compound represented by     formula (I) or a pharmaceutically acceptable salt thereof:

-   -   or a pharmaceutically acceptable salt thereof,     -   wherein R¹, R², R³, and R⁴ are each independently a group         selected from the group consisting of:     -   hydrogen,     -   hydroxyl,     -   halogen,     -   cyano,     -   nitro,     -   amino,     -   C₁-C₆ alkyl,     -   C₂-C₆ alkenyl,     -   C₂-C₆ alkynyl,     -   C₃-C₁₀ cycloalkyl,     -   C₃-C₁₀ cycloalkenyl,     -   C₁-C₆ alkoxy,     -   C₆-C₁₀ aryl,     -   indanyl,     -   heteroaryl,     -   3- to 8-membered heterocycloalkyl,     -   —OSO₂CH₃,     -   —OSO₂CF₃, and     -   —CONH₂,     -   wherein each of the groups of R¹ to R⁴ is optionally substituted         with a substituent selected from the group consisting of         substituent A below:     -   substituent A:         -   hydroxyl;         -   oxo (═O);         -   cyano;         -   halogen;         -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally             substituted with a substituent selected from the group             consisting of substituent B below);         -   C₃-C₁₀ cycloalkyl [wherein the C₃-C₁₀ cycloalkyl is             optionally substituted with cyano, or C₁-C₆ alkyl             substituted with —NR³¹R³² (wherein R³¹ and R³² each             independently represent hydrogen or C₁-C₆ alkyl)];         -   —NR²¹R²² [wherein R²¹ and R²² each independently represent             hydrogen, or C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is             optionally substituted with di(C₁-C₆ alkyl)amino, C₁-C₆             alkylsulfonyl (—SO₂(C₁-C₆ alkyl)), or 3- to 8-membered             heterocycloalkyl)];         -   C₁-C₆ alkoxy {wherein the C₁-C₆ alkoxy is optionally             substituted with halogen, 3- to 8-membered heterocycloalkyl             (wherein the 3- to 8-membered heterocycloalkyl is optionally             substituted with C₁-C₆ alkyl), or —NR³³R³⁴ [wherein R³³ and             R³⁴ each independently represent hydrogen, C₁-C₆ alkyl             (wherein the C₁-C₆ alkyl is optionally substituted with             C₁-C₆ alkylsulfonyl or di(C₁-C₆ alkyl)amino), or C₁-C₆             alkylsulfonyl]};         -   —SO₂NR²³R²⁴ {wherein R²³ and R²⁴ each independently             represent hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is             optionally substituted with hydroxyl, C₁-C₆ alkoxy, halogen,             C₃-C₁₀ cycloalkyl, or —NR³⁵R³⁶ (wherein R³⁵ and R³⁶ each             independently represent hydrogen or C₁-C₆ alkyl)], C₃-C₁₀             cycloalkyl (wherein the C₃-C₁₀ cycloalkyl is optionally             substituted with C₁-C₆ hydroxyalkyl), or 3- to 8-membered             heterocycloalkyl; or R²³ and R²⁴ may together form 3- to             8-membered heterocycloalkyl wherein the 3- to 8-membered             heterocycloalkyl is optionally substituted with amino};         -   C₁-C₆ alkylsulfonyl (wherein the C₁-C₆ alkyl moiety is             optionally substituted with hydroxyl);         -   C₁-C₆ alkylsulfonylamino (—NHSO₂(C₁-C₆ alkyl)) [wherein the             C₁-C₆ alkyl moiety is optionally substituted with —NR³⁷R³⁸             (wherein R³⁷ and R³⁸ each independently represent hydrogen             or C₁-C₆ alkyl)];         -   3- to 8-membered heterocycloalkyl {wherein the 3- to             8-membered heterocycloalkyl is optionally substituted with             —NR³⁹R⁴⁰ (wherein R³⁹ and R⁴⁰ each independently represent             hydrogen, C₁-C₆ alkyl, or C₁-C₆ alkylsulfonyl), C₁-C₆ alkyl             [wherein the C₁-C₆ alkyl is optionally substituted with             —NR⁴¹R⁴² (wherein R⁴¹ and R⁴² each independently represent             hydrogen or C₁-C₆ alkyl)], hydroxyl, or C₁-C₆             alkylsulfonyl};         -   heteroaryl;         -   —COOR¹¹ (wherein R¹¹ represents hydrogen or C₁-C₆ alkyl);             and         -   —COR¹² [wherein R¹² represents C₁-C₆ alkyl, C₃-C₁₀             cycloalkyl, cyanomethyl, —NR²⁵R²⁶ {wherein R²⁵ and R²⁶ each             independently represent hydrogen, or C₁-C₆ alkyl [wherein             the C₁-C₆ alkyl is optionally substituted with hydroxyl or             —NR⁴³R⁴⁴ (wherein R⁴³ and R⁴⁴ each independently represent             hydrogen or C₁-C₆ alkyl)]}, or 3- to 8-membered             heterocycloalkyl which is optionally substituted with C₁-C₆             alkyl],     -   substituent B:         -   halogen;         -   hydroxyl;         -   cyano;         -   3- to 8-membered heterocycloalkyl (wherein the 3- to             8-membered heterocycloalkyl is optionally substituted with             C₁-C₆ alkyl, hydroxyl, amino, C₁-C₆ aminoalkyl, or C₁-C₆             alkyl substituted with C₂-C₇ alkyloxycarbonylamino);         -   —NR⁵¹R⁵² (wherein R⁵¹ and R⁵² each independently represent             hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is optionally             substituted with C₁-C₆ alkylsulfonyl, or 3- to 8-membered             heterocycloalkyl optionally substituted with —COOR¹³             (wherein R⁵³ represents hydrogen or C₁-C₆ alkyl)], 3- to             8-membered heterocycloalkyl, C₁-C₆ alkylsulfonyl, C₃-C₁₀             cycloalkyl, —COR⁵⁵ (wherein R⁵⁵ represents C₁-C₆ alkyl),             —COOR⁵⁶ (wherein R⁵⁶ represents C₁-C₆ alkyl), or —CONR⁵⁷R⁵⁸             (wherein R⁵⁷ and R⁵⁸ each independently represent hydrogen             or C₁-C₆ alkyl)); and         -   —COOR⁵⁴ (wherein R⁵⁴ represents hydrogen or C₁-C₆ alkyl)];     -   wherein R⁵ is hydrogen or C₁-C₆ alkyl; and     -   wherein

-   -    is a structure selected from the group consisting of         -   (i) —S—CR⁷═CR⁶—,         -   (ii) —CH₂—CH₂—CH₂—,         -   (iii) —NH—CH═CCH₃—, and         -   (iv) —═CH—S—,     -   wherein R⁶ is         -   hydrogen,         -   hydroxyl,         -   C₁-C₆ alkyl,         -   C₆-C₁₀ aryl (wherein the C₆-C₁₀ aryl is optionally             substituted with hydroxyl), or         -   3- to 8-membered heterocycloalkyl [wherein the 3- to             8-membered heterocycloalkyl is optionally substituted with             —NR⁶¹R⁶² (wherein R⁶¹ and R⁶² each independently represent             hydrogen or C₁-C₆ alkyl)], and     -   wherein R⁷ is         -   hydrogen,         -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally             substituted with hydroxyl, —NR⁷¹R⁷² [wherein R⁷¹ and R⁷²             each independently represent hydrogen, C₁-C₆ alkyl (wherein             the C₁-C₆ alkyl is optionally substituted with             dimethylamino), C₃-C₁₀ cycloalkyl (wherein the C₃-C₁₀             cycloalkyl is optionally substituted with amino), or 3- to             8-membered heterocycloalkyl], or 3- to 8-membered             heterocycloalkyl (wherein the 3- to 8-membered             heterocycloalkyl is optionally substituted with C₁-C₆             aminoalkyl)),         -   C₆-C₁₀ aryl (wherein the C₆-C₁₀ aryl is optionally             substituted with hydroxyl), or         -   —COR⁷³ {wherein R⁷³ represents 3- to 8-membered             heterocycloalkyl (wherein the 3- to 8-membered             heterocycloalkyl is optionally substituted with amino), or             —NR⁷⁴R⁷⁵ [wherein R⁷⁴ and R⁷⁵ each independently represent             hydrogen, 3- to 8-membered heterocycloalkyl, or C₃-C₁₀             cycloalkyl (wherein the C₃-C₁₀ cycloalkyl is optionally             substituted with amino)]}.

-   102. The compound of above 101, or a pharmaceutically acceptable     salt thereof, wherein

-    is —S—CR⁷═CR⁶—.     -   Specifically, the compound of above 1 which have a following         formula II, or a pharmaceutically acceptable salt thereof;

-   103. The compound of above 102, or a pharmaceutically acceptable     salt thereof, wherein R¹ is hydrogen or halogen. -   104. The compound of above 102 or 103, or a pharmaceutically     acceptable salt thereof, wherein R² is hydrogen, hydroxyl, halogen,     C₁-C₆ alkoxy, or C₆-C₁₀ aryl which is optionally substituted with     hydroxyl. -   105. The compound of any one of above 102-104 or a pharmaceutically     acceptable salt, wherein R² is hydrogen, hydroxyl, halogen, C₁-C₆     alkoxy, or dihydroxyphenyl. -   106. The compound of any one of above 102-105, or a pharmaceutically     acceptable salt thereof, wherein R³ is hydrogen; hydroxyl; halogen;     C₁-C₆ alkoxy; cyano; nitro; 3- to 8-membered heterocycloalkyl which     is optionally substituted with amino; heteroaryl; —OSO₂CH₃;     —OSO₂CF₃; or —CONH₂. -   107. The compound of any one of above 102-106, or a pharmaceutically     acceptable salt thereof, wherein R³ is hydrogen; hydroxyl; halogen;     C₁-C₆ alkoxy; cyano; nitro; 3- to 8-membered heterocycloalkyl which     is optionally substituted with amino (wherein the 3- to 8-membered     heterocycloalkyl is piperidyl, pyrrolidinyl, morpholinyl, or     piperazinyl); pyridyl; —OSO₂CH₃; —OSO₂CF₃; or —CONH₂. -   108. The compound of any one of above 102-107, or a pharmaceutically     acceptable salt thereof, wherein R⁴ is a group selected from the     group consisting of hydrogen, hydroxyl, halogen, amino, C₁-C₆ alkyl,     C₂-C₆ alkenyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₁-C₆ alkoxy,     C₆-C₁₀ aryl, indanyl, heteroaryl, and 3- to 8-membered     heterocycloalkyl, wherein each of the groups of R⁴ is optionally     substituted with a substituent selected from the group consisting of     substituent A above. -   109. The compound of any one of above 102-108, or a pharmaceutically     acceptable salt thereof, wherein R⁴ is a group selected from the     group consisting of hydrogen, hydroxyl, halogen, amino, C₁-C₆ alkyl,     C₂-C₆ alkenyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₁-C₆ alkoxy,     C₆-C₁₀ aryl, indanyl, heteroaryl (wherein the heteroaryl is selected     from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl,     [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl,     2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl,     pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl),     and 3- to 8-membered heterocycloalkyl (wherein the 3- to 8-membered     heterocycloalkyl is selected from the group consisting of     aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidyl,     piperazinyl, azepanyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl),     wherein each of the groups of R⁴ is optionally substituted with a     substituent selected from the group consisting of substituent A-1     below:     -   substituent A-1:     -   hydroxyl;     -   oxo;     -   cyano;     -   halogen;     -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally substituted         with a substituent selected from the group consisting of         substituent B-1 below);     -   C₃-C₁₀ cycloalkyl [wherein the C₃-C₁₀ cycloalkyl is optionally         substituted with cyano, or C₁-C₆ alkyl substituted with —NR³¹R³²         (wherein R³¹ and R³² each independently represent hydrogen or         C₁-C₆ alkyl)];     -   —NR^(21A)R^(22A) [wherein R^(21A) and R^(22A) each independently         represent hydrogen or C₁-C₆ alkyl (wherein C₁-C₆ alkyl is         optionally substituted with di(C₁-C₆ alkyl)amino, C₁-C₆         alkylsulfonyl (—SO₂ (C₁-C₆ alkyl)), or piperidyl)];     -   C₁-C₆ alkoxy {wherein the C₁-C₆ alkoxy is optionally substituted         with 3- to 8-membered heterocycloalkyl selected from halogen,         piperidyl, and piperazinyl (wherein the 3- to 8-membered         heterocycloalkyl is optionally substituted with C₁-C₆ alkyl), or         —NR³³R³⁴ [wherein R³³ and R³⁴ each independently represent         hydrogen, C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally         substituted with C₁-C₆ alkylsulfonyl or di(C₁-C₆ alkyl)amino),         or C₁-C₆ alkylsulfonyl]};     -   —SO₂NR^(23A)R^(24A) {wherein R^(23A) and R^(24A) each         independently represent hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆         alkyl is optionally substituted with hydroxyl, C₁-C₆ alkoxy,         halogen, C₃-C₁₀ cycloalkyl, or —NR³⁵R³⁶ (wherein R³⁵ and R³⁶         each independently represent hydrogen or C₁-C₆ alkyl)], C₃-C₁₀         cycloalkyl (wherein the C₃-C₁₀ cycloalkyl is optionally         substituted with C₁-C₆ hydroxyalkyl), azetidinyl, or         pyrrolidinyl, or may together form pyrrolidinyl, wherein the         pyrrolidinyl is optionally substituted with amino};     -   C₁-C₆ alkylsulfonyl (wherein the C₁-C₆ alkyl moiety is         optionally substituted with hydroxyl);     -   C₁-C₆ alkylsulfonylamino (—NHSO₂ (C₁-C₆ alkyl)) [wherein the         C₁-C₆ alkyl moiety is optionally substituted with —NR³⁷R³⁸         (wherein R³⁷ and R³⁸ each independently represent hydrogen or         C₁-C₆ alkyl)];     -   3- to 8-membered heterocycloalkyl selected from the group         consisting of azetidinyl, pyrrolidinyl, piperidyl, and         piperazinyl (wherein the 3- to 8-membered heterocycloalkyl is         optionally substituted with —NR³⁹R⁴⁰ (wherein R³⁹ and R⁴⁰ each         independently represent hydrogen, C₁-C₆ alkyl, or C₁-C₆         alkylsulfonyl), C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is         optionally substituted with —NR⁴¹R⁴² (wherein R⁴¹ and R⁴² each         independently represent hydrogen or C₁-C₆ alkyl)], hydroxyl, or         C₁-C₆ alkylsulfonyl);     -   1H-tetrazolyl;     -   —COOR¹¹ (wherein R¹¹ represents hydrogen or C₁-C₆ alkyl); and     -   —COR^(12A) [wherein R^(12A) represents piperazinyl which is         optionally substituted with C₁-C₆ alkyl, C₃-C₁₀ cycloalkyl,         cyanomethyl, —NR²⁵R²⁶ {wherein R²⁵ and R²⁶ each independently         represent hydrogen or C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is         optionally substituted with hydroxyl or —NR⁴³R⁴⁴ (wherein R⁴³         and R⁴⁴ each independently represent hydrogen or C₁-C₆         alkyl)]}), or C₁-C₆ alkyl];     -   substituent B-1:     -   halogen;     -   hydroxyl;     -   50 cyano;     -   3- to 8-membered heterocycloalkyl selected from the group         consisting of pyrrolidinyl, piperidyl, piperazinyl, and         morpholinyl (wherein the 3- to 8-membered heterocycloalkyl is         optionally substituted with C₁-C₆ alkyl, hydroxyl, amino, C₁-C₆         aminoalkyl, or C₁-C₆ alkyl substituted with C₂-C₇         alkyloxycarbonylamino);     -   —NR^(51A)R^(52A) {wherein R^(51A) and R^(52A) each independently         represent hydrogen, C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is         optionally substituted with C₁-C₆ alkylsulfonyl, or piperidyl         which is optionally substituted with, —COOR¹³ (wherein R⁵³         represents hydrogen or C₁-C₆ alkyl)], piperidyl, C₁-C₆         alkylsulfonyl, C₃-C₁₀ cycloalkyl, —COR⁵⁵ (wherein R⁵⁵ represents         C₁-C₆ alkyl), —COOR⁵⁶ (wherein R⁵⁶ represents C₁-C₆ alkyl), or         —CONR⁵⁷R⁵⁸ (wherein R⁵⁷ and R⁵⁸ each independently represent         hydrogen or C₁-C₆ alkyl)}; and     -   —COOR⁵⁴ (wherein R⁵⁴ represents hydrogen or C₁-C₆ alkyl). -   1010. The compound of any one of above 102-109, or a     pharmaceutically acceptable salt thereof, wherein R⁴ is a group     selected from the group consisting of (p) below:     -   (p):         -   hydrogen,         -   hydroxyl,         -   halogen,         -   amino,         -   C₁-C₆ alkyl which is optionally substituted with a             substituent selected from the group consisting of             substituent (a) below,         -   C₂-C₆ alkenyl which is optionally substituted with a             substituent selected from the group consisting of             substituent (b) below,         -   C₃-C₁₀ cycloalkyl,         -   C₃-C₁₀ cycloalkenyl,         -   C₁-C₆ alkoxy,         -   C₆-C₁₀ aryl which is optionally substituted with a             substituent selected from the group consisting of             substituent (c) below,         -   indanyl which is optionally substituted with a substituent             selected from the group consisting of substituent (d) below,         -   heteroaryl which is optionally substituted with a             substituent selected from the group consisting of             substituent (e) below, and         -   3- to 8-membered heterocycloalkyl which is optionally             substituted with a substituent selected from the group             consisting of substituent (f) below, wherein, in the group             (p),         -   the heteroaryl is selected from the group consisting of             pyridyl, 1H-indazolyl, 1H-tetrazolyl,             [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl,             2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl,             pyrimidinyl, indolinyl, furyl, thienyl, and             tetrahydroisoquinolyl;         -   the 3- to 8-membered heterocycloalkyl is selected from the             group consisting of pyrrolidinyl, piperidyl, piperazinyl,             morpholinyl, and 1,2,3,6-tetrahydropyridyl;         -   substituent (a):             -   3- to 8-membered heterocycloalkyl selected from the                 group consisting of pyrrolidinyl and piperidyl {wherein                 the 3- to 8-membered heterocycloalkyl is optionally                 substituted with —NR³⁹R⁴⁰ (wherein R³⁹ and R⁴⁰ each                 independently represent hydrogen or C₁-C₆ alkyl), or                 C₁-C₆ alkyl [wherein the C₁-C₆ alkyl is optionally                 substituted with —NR⁴¹R⁴² (wherein R⁴¹ and R⁴² each                 independently represent hydrogen or C₁-C₆ alkyl)]}; and             -   C₁-C₆ alkylsulfonylamino (—NHSO₂(C₁-C₆ alkyl));         -   substituent (b):             -   —COOR¹¹ (wherein R¹¹ represents hydrogen or C₁-C₆                 alkyl);             -   —NR^(21a)R^(22a) [wherein R^(21a) and R^(22a) each                 independently represent hydrogen, or C₁-C₆ alkyl                 (wherein the C₁-C₆ alkyl is optionally substituted with                 di(C₁-C₆ alkyl)amino or C₁-C₆ alkylsulfonyl)];             -   3- to 8-membered heterocycloalkyl selected from the                 group consisting of azetidinyl, pyrrolidinyl, and                 piperidyl (wherein the 3- to 8-membered heterocycloalkyl                 is optionally substituted with —NR³⁹R⁴⁰ {wherein R³⁹ and                 R⁴⁰ each independently represent hydrogen, C₁-C₆ alkyl,                 or C₁-C₆ alkylsulfonyl), C₁-C₆ alkyl [wherein the C₁-C₆                 alkyl is optionally substituted with —NR⁴¹R⁴² (wherein                 R⁴¹ and R⁴² each independently represent hydrogen or                 C₁-C₆ alkyl)], hydroxyl, or C₁-C₆ alkylsulfonyl};             -   cyano; and             -   C₁-C₆ alkoxy;         -   substituent (c):             -   hydroxyl;             -   cyano;             -   halogen;             -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally                 substituted with a substituent selected from the group                 consisting of substituent B-c below);             -   C₃-C₁₀ cycloalkyl [wherein the C₃-C₁₀ cycloalkyl is                 optionally substituted with cyano, or C₁-C₆ alkyl                 substituted with —NR³¹R³² (wherein R³¹ and R³² each                 independently represent hydrogen or C₁-C₆ alkyl)];             -   —NR^(21c)R^(22c) [wherein R^(21c) and R^(22c) each                 independently represent hydrogen or C₁-C₆ alkyl];             -   C₁-C₆ alkoxy {wherein the C₁-C₆ alkoxy is optionally                 substituted with 3- to 8-membered heterocycloalkyl                 selected from halogen, piperidyl, and piperazinyl                 (wherein the 3- to 8-membered heterocycloalkyl is                 optionally substituted with C₁-C₆ alkyl), or —NR³³R³⁴                 [wherein R³³ and R³⁴ each independently represent                 hydrogen, C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is                 optionally substituted with di(C₁-C₆ alkyl)amino), or                 C₁-C₆ alkylsulfonyl]};             -   —SO₂NR^(23c)R^(24c) {wherein R^(23c) and R^(24c) each                 independently represent hydrogen, C₁-C₆ alkyl [wherein                 the C₁-C₆ alkyl is optionally substituted with hydroxyl,                 C₁-C₆ alkoxy, halogen, C₃-C₁₀ cycloalkyl, or —NR³⁵R³⁶                 (wherein R³⁵ and R³⁶ each independently represent                 hydrogen or C₁-C₆ alkyl)], C₃-C₁₀cycloalkyl (wherein the                 C₃-C₁₀ cycloalkyl is optionally substituted with C₁-C₆                 hydroxyalkyl), azetidinyl, or pyrrolidinyl, or wherein                 R^(23c) and R^(24c) may together form pyrrolidinyl which                 is optionally substituted with amino};             -   C₁-C₆ alkylsulfonyl (wherein the C₁-C₆ alkyl moiety is                 optionally substituted with hydroxyl);             -   C₁-C₆ alkylsulfonylamino (—NHSO₂(C₁-C₆ alkyl)) [wherein                 the C₁-C₆ alkyl moiety is optionally substituted with                 —NR³⁷R³⁸ (wherein R³⁷ and R³⁸ each independently                 represent hydrogen or C₁-C₆ alkyl)];             -   piperazinyl {wherein the piperazinyl is optionally                 substituted with C₁-C₆ alkyl or C₁-C₆ alkylsulfonyl};             -   1H-tetrazolyl; and             -   —COR^(12c) [wherein R^(12c) represents piperazinyl which                 is optionally substituted with C₁-C₆ alkyl, C₃-C₁₀                 cycloalkyl, cyanomethyl, —NR²⁵R²⁶ {wherein R²⁵ and R²⁶                 each independently represent hydrogen or C₁-C₆ alkyl                 [wherein the C₁-C₆ alkyl is optionally substituted with                 hydroxyl, or —NR⁴³R⁴⁴ (wherein R⁴³ and R⁴⁴ each                 independently represent hydrogen or C₁-C₆ alkyl)]}), or                 C₁-C₆ alkyl]; and         -   substituent B-c:             -   halogen;             -   hydroxyl;             -   cyano;             -   3- to 8-membered heterocycloalkyl selected from the                 group consisting of pyrrolidinyl, piperidyl,                 piperazinyl, and morpholinyl (wherein the 3- to                 8-membered heterocycloalkyl is optionally substituted                 with C₁-C₆ alkyl, hydroxyl, amino, C₁-C₆ aminoalkyl, or                 C₁-C₆ alkyl substituted with C₂-C₇                 alkyloxycarbonylamino); and             -   —NR^(51c)R^(52c) {wherein R^(51c) and R^(52c) each                 independently represent hydrogen, C₁-C₆ alkyl [wherein                 the C₁-C₆ alkyl is optionally substituted with C₁-C₆                 alkylsulfonyl, or piperidyl which is optionally                 substituted with —COOR⁵³ (wherein R⁵³ represents                 hydrogen or C₁-C₆ alkyl)], piperidyl,                 C₁-C₆alkylsulfonyl, C₃-C₁₀cycloalkyl, —COR⁵⁵ (wherein                 R⁵⁵ represents C₁-C₆ alkyl), or —CONR⁵⁷R⁵⁸ (wherein R⁵⁷                 and R⁵⁸ each independently represent hydrogen or C₁-C₆                 alkyl)}];         -   substituent (d):             -   —NR^(21d)R^(22d) (wherein R^(21d) and R^(22d) each                 independently represent hydrogen or C₁-C₆ alkyl);         -   substituent (e):             -   hydroxyl;             -   oxo;             -   cyano;             -   —NR²¹R²² [wherein R²¹ and R²² each independently                 represent hydrogen or C₁-C₆ alkyl];             -   piperidyl;             -   C₁-C₆ alkoxy; and             -   C₁-C₆ alkyl {wherein the C₁-C₆ alkyl is optionally                 substituted with —NR^(51e)R^(52e) [wherein R^(51e) and                 R^(52e) each independently represent hydrogen or —COOR⁵⁶                 (wherein R⁵⁶ represents C₁-C₆ alkyl)]}); and         -   substituent (f):             -   C₁-C₆ alkyl {wherein the C₁-C₆ alkyl is optionally                 substituted with —NR^(51f)R^(52f) [wherein R^(51f) and                 R^(52f) each independently represent hydrogen, C₁-C₆                 alkyl, or —COOR⁵⁶ (wherein R⁵⁶ represents C₁-C₆                 alkyl)]}; and             -   C₁-C₆ alkylsulfonyl. -   111. The compound of any one of above 102-110, or a pharmaceutically     acceptable salt thereof, wherein R⁶ is hydrogen; hydroxyl; C₁-C₆     alkyl; phenyl which is optionally substituted with 1 to 3 hydroxyls;     piperidyl which is optionally substituted with amino; or     piperazinyl. -   112. The compound of above 111, or a pharmaceutically acceptable     salt thereof, wherein R⁷ is hydrogen. -   113. The compound of any one of above 102-111, or a pharmaceutically     acceptable salt thereof, wherein R⁷ is     -   hydrogen;     -   C₁-C₆ alkyl (wherein the C₁-C₆ alkyl is optionally substituted         with hydroxyl, —NR^(71A)R^(72A) [wherein R^(71A) and R^(72A)         each independently represent hydrogen, C₁-C₆ alkyl (wherein the         C₁-C₆ alkyl is optionally substituted with dimethylamino),         C₃-C₁₀ cycloalkyl (wherein the C₃-C₁₀ cycloalkyl is optionally         substituted with amino), or piperidyl], or 3- to 8-membered         heterocycloalkyl selected from the group consisting of piperidyl         and morpholinyl (wherein the 3- to 8-membered heterocycloalkyl         is optionally substituted with C₁-C₆ aminoalkyl));     -   phenyl which is optionally substituted with 1 to 2 hydroxyls; or     -   —COR^(73A) {wherein R^(73A) represents piperidyl (wherein the         piperidyl is optionally substituted with amino), or         —NR^(74A)R^(75A) [wherein R^(74A) and R^(75A) each independently         represent hydrogen, piperidyl, or C₃-C₁₀ cycloalkyl (wherein the         C₃-C₁₀ cycloalkyl is optionally substituted with amino)]}. -   114. The compound of above 101, or a pharmaceutically acceptable     salt thereof, wherein

-    is —CH₂—CH₂—CH₂—.     -   Specifically, the compound of above 1 which have a following         formula III, or a pharmaceutically acceptable salt thereof:

-   115. The compound of above 114, or a pharmaceutically acceptable     salt thereof, wherein R¹, R² and R⁵ are hydrogen. -   116. The compound of above 114 or 115, or a pharmaceutically     acceptable salt thereof, wherein R³ is hydroxyl or methoxy. -   117. The compound of any one of above 114-116, or a pharmaceutically     acceptable salt thereof, wherein R⁴ is hydrogen, phenyl [wherein the     phenyl is substituted with C₁-C₆ alkyl substituted with     —NR^(51A)R^(52A) (wherein R^(51A) and R^(52A) each independently     represent hydrogen or C₁-C₆ alkyl), or —SO₂NH₂],     1,2,3,6-tetrahydropyridyl, hydroxypyridyl, or methoxypyridyl. -   118. The compound of above 101, or a pharmaceutically acceptable     salt thereof, wherein

-    is —NH—CH═CCH₃—,     -   R¹, R², R⁴ and R⁵ are hydrogen, and     -   R³ is hydroxyl. -   119. The compound of above 101, or a pharmaceutically acceptable     salt thereof, wherein

-    is —N═CH—S—,     -   R¹, R², R⁴ and R⁵ are hydrogen, and     -   R³ is methoxy. -   120. A compound selected from the group consisting of: -   (1): 8-methoxy-5-methylthieno[2,3-c]quinolin-4(5H)-one; -   (2): 8-hydroxy-5-methylthieno[2,3-c]quinolin-4(5H)-one; -   (3): 7,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one; -   (4): 7,8-dimethoxythieno[2,3-c]quinolin-4(5H)-one; -   (5): 8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (6): 7,9-dimethoxythieno[2,3-c]quinolin-4(5H)-one; -   (7): 7,9-dihydroxythieno[2,3-c]quinolin-4(5H)-one; -   (8): 7,8,9-trimethoxythieno[2,3-c]quinolin-4(5H)-one; -   (9): 8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (10): 7,8,9-trihydroxythieno[2,3-c]quinolin-4(5H)-one; -   (11):     9-(3-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (12): 8-chlorothieno[2,3-c]quinolin-4(5H)-one; -   (13): 4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; -   (14): thieno[2,3-c]quinolin-4(5H)-one; -   (15): 8-fluorothieno[2,3-c]quinolin-4(5H)-one; -   (16): 8-nitrothieno[2,3-c]quinolin-4(5H)-one; -   (17): 8-(3-aminopiperidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (18): 1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (19): 1,8-dihydroxythieno[2,3-c]quinolin-4(5H)-one; -   (20): 8-hydroxy-1-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (2H): (R)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (22): (S)-8-(3-aminopyrrolidin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (23): 8-(pyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (24): 8-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (25):     1-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (26):     1-(3-aminopiperidin-1-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (27): 8-morpholinothieno[2,3-c]quinolin-4(5H)-one; -   (28): 8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one; -   (29): 8-hydroxy-2-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (30):     8-hydroxy-4-oxo-N-(piperidin-3-yl)-4,5-dihydrothieno[2,3-c]quinoline-2-carboxamide; -   (31): 8-hydroxy-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (32): 8-hydroxy-1-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (33):     N-((1r,4r)-4-aminocyclohexyl)-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-2-carboxamide; -   (34):     2-(3-aminopiperidine-1-carbonyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (35):     2-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (36):     2-(((1r,4r)-4-aminocyclohexylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (37): 8-(piperazin-1-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (38): 8-hydroxy-1-methylthieno[2,3-c]quinolin-4(5H)-one; -   (39):     2-((2-(dimethylamino)ethylamino)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (40):     8-hydroxy-2-((piperidin-3-ylamino)methyl)thieno[2,3-c]quinolin-4(5H)-one; -   (41): 7-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (42): 9-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (43):     9-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (44):     1-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; -   (45):     7-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (46): 8-hydroxy-1-methyl-3H-pyrrolo[2,3-c]quinolin-4(5H)-one; -   (47):     9-(3,5-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (48): 8-hydroxy-9-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (49): 8-hydroxy-9-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (50):     9-(3,4-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (51):     (S)-8-(3-aminopyrrolidin-1-yl)-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (52):     5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)picolinonitrile; -   (53):     9-(6-aminopyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (54):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (55):     9-(3-fluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (56): 8-hydroxy-2-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (57):     (R)-8-(3-aminopyrrolidin-1-yl)-2-(3,4-dihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (58):     9-(3,4-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (59):     9-(4-fluoro-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (60):     8-hydroxy-9-(3-hydroxy-5-(trifluoromethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (61): 8-hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (62):     8-hydroxy-9-(3,4,5-trihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (63): 9-(4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (64):     9-(4-(1H-tetrazol-5-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (65):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (66):     9-(3-chloro-4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (67):     9-(4-chloro-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (68):     9-(3,4-dichlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (69): 9-(4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (70): 8-hydroxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one; -   (71):     9-(4-(difluoromethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (72):     9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (73):     9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (74): 9-(3-aminophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (75):     3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (76):     8-hydroxy-9-(3,4,5-trifluorophenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (77):     N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (78): 8-methoxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one; -   (79): 8-hydroxy-9-(naphthalen-2-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (80):     8-hydroxy-9-(4-(hydroxymethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (81):     2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (82):     8-hydroxy-9-(4-(methylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (83): 8-hydroxy-9-(pyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (84):     8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (85):     8-hydroxy-9-(4-hydroxy-3-methoxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (86):     9-(3-fluoro-4-(morpholinomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (87):     9-(3-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (88):     9-(4-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (89):     9-(3-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (90):     9-(3-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one; -   (91): 9-cyclohexenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (92):     9-(3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (93):     9-(4-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (94):     9-(3-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (95):     9-(4-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one; -   (96): 9-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (97):     9-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (98):     8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (99): 9-cyclohexenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (100):     8-methoxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (101):     9-(4-(aminomethyl)phenyl)-8-hydroxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (102):     9-(1H-benzo[d]imidazol-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (103):     9-(4-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (104):     9-(4-(aminomethyl)phenyl)-8-methoxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one; -   (105):     8-hydroxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (106):     8-hydroxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (107): 8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (108): 8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (109):     5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzo[d]oxazol-2(3H)-one; -   (110): tert-butyl     4-(2-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylamino)ethyl)piperidin-1-carboxylate; -   (111):     8-methoxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (112):     8-hydroxy-9-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (113):     8-hydroxy-9-(4-((piperidin-3-ylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (114):     N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (115):     9-(4-(3-(dimethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-(5H)-one; -   (116):     8-methoxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (117):     8-hydroxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (118): 8-methoxythiazolo[4,5-c]quinolin-4(5H)-one; -   (119):     2-((4-(aminomethyl)piperidin-1-yl)methyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (120):     N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (121):     9-(4-(aminomethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (122): (E)-butyl     3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)acrylate; -   (123):     8-methoxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (124):     8-hydroxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (125):     N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide; -   (126):     N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (127):     N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (128):     N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide; -   (129):     4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide; -   (130):     8-hydroxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (131):     8-methoxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (132):     8-hydroxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (133):     8-methoxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (134):     (E)-9-(3-(diethylamino)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (135):     (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (136):     (E)-9-(3-(2-(diethylamino)ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (137):     N-(4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)phenyl)methanesulfonamide; -   (138):     9-(2-(dimethylamino)pyrimidin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (139): tert-butyl     (1-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)piperidin-4-yl)methylcarbamate; -   (140):     8-hydroxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (141):     8-methoxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (142):     8-methoxy-9-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (143):     (E)-9-(3-(diethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (144):     9-(3-(4-(aminomethyl)piperidin-1-yl)propyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (145):     9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (146):     9-(4-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (147):     9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (148):     (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (149):     9-(4-(3-(dimethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (150):     8-hydroxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (151):     9-(4-(2-(ethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one; -   (152):     (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (153):     9-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (154):     9-(4-(2-(ethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (155):     9-(4-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (156):     9-(4-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (157):     9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (158):     9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (159):     8-methoxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (160):     8-methoxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (161):     9-(3-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (162):     9-(3-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (163):     9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (164):     9-(4-((dimethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (165):     9-(4-((dimethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (166):     9-(3-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (167):     8-hydroxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (168):     N-ethyl-N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylmethoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenoxy)ethyl)methanesulfonamide; -   (169):     9-(4-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (170):     2-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (171):     2-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (172):     9-(1-(2-(dimethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (173):     N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (174):     9-(1-(2-(diethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (175):     9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (176):     9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (177):     N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (178):     N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (179):     N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (180):     8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (181):     9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (182):     9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (183):     9-(4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (184):     9-(4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (185):     9-(3-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (186):     9-(3-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (187):     8-hydroxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (188):     8-methoxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (189):     9-(4-amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (190): 3-(8-hydroxy-4     oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile; -   (191):     9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (192):     9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (193):     N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide; -   (194):     8-hydroxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (195):     9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (196):     9-(4-(1-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (197):     N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (198):     N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (199):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(pyrrolidin-3-yl)benzenesulfonamide; -   (200):     N-(azetidin-3-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (201):     9-(4-(2-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (202):     2-amino-N-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; -   (203): 4-(8-hydroxy-4     oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile; -   (204): 4-(8-methoxy-4     oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile; -   (205):     (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (206):     N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide; -   (207):     8-methoxy-9-(5-methoxypyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (208):     8-methoxy-9-(5-methoxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (209):     9-(4-(3-aminopyrrolidin-1-ylsulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (210):     N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzensulfonamide; -   (211):     9-(4-((diisopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (212):     N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)methanesulfonamide; -   (213):     9-(4-((isopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (214):     2-(dimethylamino)-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; -   (215):     2-amino-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; -   (216):     8-methoxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (217):     9-(4-amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (218):     N-(2-methoxy-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (219):     9-(3,5-difluoro-4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (220):     N-(2-hydroxy-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; -   (221):     9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (222):     9-(4-(2-(dimethylamino)ethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (223):     9-(3,5-difluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (224):     6-fluoro-8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (225):     9-(4-(1-(dimethylamino)ethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-(5H)-one; -   (226):     9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (227):     (E)-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (228):     (E)-8-hydroxy-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one -   (229):     8-hydroxy-9-(4-((isopropylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (230):     (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (231):     (E)-8-methoxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one; -   (232):     (S)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (233):     (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (234):     8-hydroxy-9-(5-hydroxypyridin-3-yl)-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one; -   (235):     9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (236):     8-methoxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (237):     9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (238):     (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (239):     (E)-9-(3-(ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (240):     9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (241):     9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (242):     9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (243):     8-hydroxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (244):     (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (245):     (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (246):     (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (247):     (E)-8-hydroxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one; -   (248):     8-methoxy-9-(4-(2-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-(5H)-one; -   (249):     2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (250):     (E)-N-(1-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl)azetidin-3-yl)methanesulfonamide; -   (251):     4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide; -   (252):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide; -   (253): tert-butyl     (5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)furan-2-yl)methylcarbamate; -   (254):     N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide; -   (255):     N-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide; -   (256):     9-(4-(aminomethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (257):     9-(4-(aminomethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (258):     6-fluoro-8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (259):     9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (260):     8-methoxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (261):     2-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; -   (262):     8-hydroxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (263):     (E)-9-(3-(3-(dimethylamino)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (264):     (E)-9-(3-(3-(dimethylamino)pyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (265):     9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (266):     9-(5-(aminomethyl)thiophen-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (267):     9-(4-((ethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (268):     (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (269):     9-(4-((ethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (270):     9-(4-(aminomethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (271):     9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (272):     (R)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (273):     9-(4-(3-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (274):     (R)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (275):     (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (276):     9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (277):     9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (278):     9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (279):     9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (280):     4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide; -   (281):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzene     sulfonamide; -   (282):     N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (283):     8-hydroxy-9-(4-((2-(methylsulfonyl)ethylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (284):     9-(3-(3-(dimethylamino)pyrrolidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (285):     9-(1-(2-aminoethyl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (286):     9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (287):     4-(7-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; -   (288): 9-(3-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (289):     2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide; -   (290):     3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (291): 9-(4-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (292):     2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (293):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide; -   (294):     1,1-diethyl-3-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)urea; -   (295):     N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; -   (296): 9-(4-acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (297):     N-(2-bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (298):     9-(3-(3-(dimethylamino)piperidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (299):     N-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (300):     9-(3-fluoro-4-(2-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     methanesulfonate; -   (301):     (R)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide; -   (302):     (R)-9-(4-(1-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     methanesulfonate; -   (303):     2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (304):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide; -   (305):     9-(4-(2-(dimethylamino)ethyl)phenyl)-7-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (306):     N-(2-bromoethyl)-4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (307):     4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; -   (308):     9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (309):     N-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)-N-methyl     methanesulfonamide; -   (310): 4-(8-hydroxy-4     oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide; -   (3H):     (E)-3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylacrylonitrile; -   (312):     N-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; -   (313):     8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (314):     9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (315):     9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (316):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; -   (317):     9-(5-(aminomethyl)furan-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (318):     9-(3-chloro-4-((methylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (319):     9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (320):     N-(3-hydroxypropyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (321):     2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; -   (322):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3-hydroxypropyl)benzenesulfonamide; -   (323):     N-(3-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (324):     2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide; -   (325):     9-(3-chloro-4-((methylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (326): 9-(4-(aminomethyl)phenyl)-4     oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; -   (327):     9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-(5H)-one; -   (328):     9-(4-(aminomethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (329):     9-(4-(aminomethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (330):     9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl     trifluoromethanesulfonate; -   (331):     9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (332):     N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (333):     N-(2-fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (334):     9-(4-(2-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (335):     (S)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (336):     9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (337):     9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (338):     9-(4-(1-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (339):     9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (340): 9-amino-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (341):     9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (342):     9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (343):     N-cyclopropyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (344):     N-cyclopropyl-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (345):     9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (346):     9-(4-(1-(dimethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (347):     (S)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide; -   (348):     9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (349):     9-(4-(1-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (350):     N-(1-(hydroxymethyl)cyclopentyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (351):     9-(2-(diethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one -   (352):     9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (353):     8-hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (354):     8-methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (355):     3-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (356):     9-(4-(1-(diethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (357): 1-(4-(8-methoxy     4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile; -   (358):     9-(2-ethyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (359):     9-(4-(1-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (360):     3-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; -   (361):     1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile; -   (362):     9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (363):     N-isopentyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (364):     9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (365):     9-(4-(1-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (366):     6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (367):     9-(4-(cyclopropanecarbonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (368):     9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carboxamide; -   (369): 9-(2-aminoethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (370):     8-hydroxy-9-(4-(2-hydroxyethylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; -   (371):     9-(4-(2-hydroxyethylsulfonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (372):     9-(1-ethylindolin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (373):     9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (374):     8-hydroxy-9-(2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (375):     9-(4-(1-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (376):     8-hydroxy-9-(1-methylindolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (377): 8-hydroxy-9-(indolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; -   (378): 9-(indolin-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (379):     9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (380): 4-(8-methoxy-4     oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-propylbenzenesulfonamide; -   (381):     N-(cyclopropylmethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzene     sulfonamide; -   (382):     N-(3,3-dimethylbutyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (383):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-isopentylbenzenesulfonamide; -   (384):     N-(3,3-dimethylbutyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; -   (385):     9-(4-(1-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; -   (386):     3-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-oxopropanenitrile; -   (387):     (E)-9-(2-ethoxyvinyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; -   (388):     N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)acetamide; -   (389):     4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide; -   (390):     4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(1-(hydroxymethyl)cyclopentyl)benzenesulfonamide; -   (391):     N-(2,2-difluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide;     -   or a pharmaceutically acceptable salt thereof. -   121. A pharmaceutical composition comprising at least one compound     of any one of above 101-120 or a pharmaceutically acceptable salt     thereof, and a pharmaceutically acceptable carrier. -   122. The pharmaceutical composition of above 121 which is available     for preventing or treating a PBK dependent disease. -   123. The pharmaceutical composition of above 122, wherein the PBK     dependent disease is cancer. -   124. A PBK inhibitor comprising at least one compound of any one of     above 101-120, or a pharmaceutically acceptable salt thereof. -   125. A method for treating a PBK dependent disease in a subject,     comprising administering to said subject an effective amount of a     compound or a pharmaceutically acceptable salt thereof of any one of     above 101-120. -   126. A compound or a pharmaceutically acceptable salt thereof of any     one of above 101-120 for use in a treatment of a PBK dependent     disease. -   127. Use of a compound of any one of above 101-120 or a     pharmaceutically acceptable salt thereof in manufacturing a     pharmaceutical composition for treating a PBK dependent disease.

Preferred compounds include those selected from the group consisting of: Example Nos. 1-391 listed in Table 1 below; and the pharmaceutically acceptable salts, prodrugs, hydrates and solvates of the forgoing compounds.

TABLE 1 (Examples 1-391) Example Structure Name 1

8-methoxy-5-methylthieno[2,3-c] quinolin-4(5H)-one 2

8-hydroxy-5-methylthieno[2,3-c] quinolin-4(5H)-one 3

7,8-dihydroxythieno[2,3-c] quinolin-4(5H)-one 4

7,8-dimethoxythieno[2,3-c] quinolin-4(5H)-one 5

8-methoxythieno[2,3-c] quinolin-4(5H)-one 6

7,9-dimethoxythieno[2,3-c] quinolin-4(5H)-one 7

7,9-dihydroxythieno[2,3-c] quinolin-4(5H)-one 8

7,8,9-trimethoxythieno[2,3-c] quinolin-4(5H)-one 9

8-hydroxythieno[2,3-c] quinolin-4(5H)-one 10

7,8,9-trihydroxythieno[2,3-c] quinolin-4(5H)-one 11

9-(3-(2-aminoethyl)phenyl)-8- methoxythieno[2,3-c] quinolin-4(5H)-one 12

8-chlorothieno[2,3-c] quinolin-4(5H)-one 13

4-oxo-4,5-dihydrothieno[2,3-c] quinoline-8-carbonitrile 14

thieno[2,3-c]quinolin-4(5H)-one 15

8-fluorothieno[2,3-c]quinolin- 4(5H)-one 16

8-nitrothieno[2,3-c]quinolin- 4(5H)-one 17

8-(3-aminopiperidin-1-yl)thieno [2,3-c]quinolin-4(5H)-one 18

l-(4-hydroxyphenyl)thieno[2,3-c] quinolin-4(5H)-one 19

1,8-dihydroxythieno[2,3-c] quinolin-4(5H)-one 20

8-hydroxy-1-(4-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one 21

(R)-8-(3-aminopyrrolidin-1-yl)thieno [2,3-c]quinolin-4(5H)-one 22

(S)-8-(3-aminopyrrolidin-1-yl)thieno [2,3-c]quinolin-4(5H)-one 23

8-(pyridin-3-yl)thieno[2,3-c] quinolin-4(5H)-one 24

8-(4-hydroxyphenyl)thieno[2,3-c] quinolin-4(5H)-one 25

1-(3,4-dihydroxyphenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 26

1-(3-aminopiperidin-1-yl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 27

8-morpholinothieno[2,3-c]quinolin- 4(5H)-one hydrochloride 28

8-hydroxy-2-methylthieno[2,3-c] quinolin-4(5H)-one 29

8-hydroxy-2-(hydroxymethyl)thieno [2,3-c]quinolin-4(5H)-one 30

8-hydroxy-4-oxo-N-(piperidin-3-yl)- 4,5-dihydrothieno[2,3-c]quinoline-2- carboxamide 31

8-hydroxy-2-(4-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one 32

8-hydroxy-1-(piperazin-1-yl)thieno [2,3-c]quinolin-4(5H)-one 33

N-((1R,4R)-4-aminocyclohexyl)-8- hydroxy-4-oxo-4,5-dihydrothieno[2,3-c] quinoline-2-carboxamide 34

2-(3-aminopiperidine-1-carbonyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 35

2-(3,4-dihydroxyphenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 36

2-(((1R,4R)-4-aminocyclohexylamino) methyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 37

8-(piperazin-1-yl)thieno[2,3-c] quinolin-4(5H)-one dihydrochloride 38

8-hydroxy-1-methylthieno[2,3-c] quinolin-4(5H)-one 39

2-((2-(dimethylamino)ethylamino) methyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 40

8-hydroxy-2-((piperidin-3-ylamino) methyl)thieno[2,3-c]quinolin- 4(5H)-one 41

7-hydroxythieno[2,3-c]quinolin- 4(5H)-one 42

9-bromo-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 43

9-(3,4-dihydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)-one 44

1-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinoline-8-carbonitrile 45

7-(3,4-dihydroxyphenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 46

8-hydroxy-1-methyl-3H-pyrrolo [2,3-c]quinolin-4(5H)-one 47

9-(3,5-dihydroxyphenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 48

8-hydroxy-9-(3-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one 49

8-hydroxy-9-(4-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one 50

9-(3,4-difluorophenyl)-8-methoxy thieno[2,3-c]quinolin-4(5H)-one 51

(S)-8-(3-aminopyrrolidin-1-yl)-2-(4- hydroxyphenyl)thieno[2,3-c]quinolin- 4(5H)-one dihydrochloride 52

5-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) picolinonitrile 53

9-(6-aminopyridin-3-yl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 54

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)benzamide 55

9-(3-fluoro-4-hydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 56

8-hydroxy-2-(3-hydroxyphenyl) thieno[2,3-c]quinolin-4(5H)-one 57

(R)-8-(3-aminopyrrolidin-1-yl)-2-(3,4- dihydroxyphenyl)thieno[2,3-c] quinolin-4(5H)-one dihydrochloride 58

9-(3,4-difluorophenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 59

9-(4-fluoro-3-hydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 60

8-hydroxy-9-(3-hydroxy-5-(trifluoro methyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 61

8-hydroxy-9-(1H-indazol-6-yl)thieno [2,3-c]quinolin-4(5H)-one 62

8-hydroxy-9-(3,4,5-trihydroxy phenyl)thieno[2,3-c]quinolin- 4(5H)-one 63

9-(4-hydroxyphenyl)-8-methoxy thieno[2,3-c]quinolin-4(5H)-one 64

9-(4-(1H-tetrazol-5-yl)phenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one 65

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzenesulfonamide 66

9-(3-chloro-4-fluorophenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one 67

9-(4-chloro-3-fluorophenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one 68

9-(3,4-dichlorophenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 69

9-(4-fluorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 70

8-hydroxy-9-phenylthieno[2,3-c] quinolin-4(5H)-one 71

9-(4-(difluoromethoxy)phenyl)-8- methoxythieno[2,3-c] quinolin-4(5H)-one 72

9-(4-(aminomethyl)phenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one 73

9-(4-(aminomethyl)phenyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 74

9-(3-aminophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 75

3-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzenesulfonamide 76

8-hydroxy-9-(3,4,5-trifluorophenyl) thieno[2,3-c]quinolin-4(5H)-one 77

N-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) methanesulfonamide 78

8-methoxy-9-phenylthieno[2,3-c] quinolin-4(5H)-one 79

8-hydroxy-9-(naphthalen-2-yl)thieno [2,3-c]quinolin-4(5H)-one 80

8-hydroxy-9-(4-(hydroxymethyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 81

2-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9- yl)phenyl)acetonitrile 82

8-hydroxy-9-(4-(methylsulfonyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 83

8-hydroxy-9-(pyridin-4-yl)thieno [2,3-c]quinolin-4(5H)-one 84

8-hydroxy-9-(1,2,3,6-tetrahydro pyridin-4-yl)thieno[2,3-c] quinolin-4(5H)-one 85

8-hydroxy-9-(4-hydroxy-3-methoxy phenyl)thieno[2,3-c]quinolin- 4(5H)-one 86

9-(3-fluoro-4-(morpholinomethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 87

9-(3-(aminomethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 88

9-(4-(aminomethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 89

9-(3-(difluoromethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 90

9-(3-(aminomethyl)phenyl)-8- hydroxy-2-methylthieno[2,3-c] quinolin-4(5H)-one 91

9-cyclohexenyl-8-methoxythieno [2,3-c]quinolin-4(5H)-one 92

9-(3,5-difluorophenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 93

9-(4-(2-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 94

9-(3-(aminomethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 95

9-(4-(aminomethyl)phenyl)-8- hydroxy-2-methylthieno[2,3-c] quinolin-4(5H)-one 96

9-cyclopropyl-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 97

9-([1,2,4]triazolo[1,5-a]pyridin-6-yl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 98

8-methoxy-9-(1,2,3,6-tetrahydro pyridin-4-yl)thieno[2,3-c] quinolin-4(5H)-one 99

9-cyclohexenyl-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 100

8-methoxy-9-(4-(2-(piperidin-1-yl) ethylamino)phenyl)thieno[2,3-c] quinolin-4(5H)-one 101

9-(4-(aminomethyl)phenyl)-8- hydroxy-2-(morpholinomethyl) thieno[2,3-c]quinolin-4(5H)-one 102

9-(1H-benzo[d]imidazol-5-yl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 103

9-(4-(difluoromethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 104

9-(4-(aminomethyl)phenyl)-8- methoxy-2-(morpholinomethyl) thieno[2,3-c]quinolin-4(5H)-one 105

8-hydroxy-9-(4-(2-(piperidin-1-yl) ethylamino)phenyl)thieno[2,3-c] quinolin-4(5H)-one 106

8-hydroxy-9-(4-(piperazin-1-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 107

8-methoxy-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one 108

8-hydroxy-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one 109

5-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)benzo [d]oxazol-2(3H)-one 110

tert-butyl 4-(2-(hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzylamino)ethyl)piperidine- 1-carboxylate 111

8-methoxy-9-(4-(piperazin-1-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 112

8-hydroxy-9-(4-(4-(methylsulfonyl) piperazin-1-yl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 113

8-hydroxy-9-(4-((piperidin-3-yl amino)methyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one 114

N-(2-(dimethylamino)ethyl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)benzamide 115

9-(4-(3-(dimethylamino)propoxy) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 116

8-methoxy-9-(1-(piperidin-4-yl)-1H- pyrazol-4-yl)thieno[2,3-c] quinolin-4(5H)-one 117

8-hydroxy-9-(1-(piperidin-4-yl)-1H- pyrazol-4-yl)thieno[2,3-c] quinolin-4(5H)-one 118

8-methoxythiazolo[4,5-c]quinolin- 4(5H)-one 119

2-((4-(aminomethyl)piperidin-1-yl) methyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 120

N-(2-(dimethylamino)ethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)benzamide 121

9-(4-(aminomethyl)phenyl)-8- hydroxy-2,3-dihydro-1H-cyclopenta [c]quinolin-4(5H)-one hydrochloride 122

(E)-butyl 3-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)acrylate 123

8-methoxy-9-(1H-pyrrolo[2,3-b] pyridin-5-yl)thieno[2,3-c]quinolin- 4(5H)-one 124

8-hydroxy-9-(1H-pyrrolo[2,3-b] pyridin-5-yl)thieno[2,3-c]quinolin- 4(5H)-one 125

N-(methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) acetamide 126

N-(2-aminoethyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzamide 127

N-(2-aminoethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzamide 128

N-(hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) acetamide 129

4-(8-hydroxy-4-oxo-2,3,4,5-tetra hydro-1H-cyclopenta[c]quinolin- 9-yl)benzenesulfonamide 130

8-hydroxy-9-(4-(4-methylpiperazine- 1-carbonyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 131

8-methoxy-9-(4-(4-methylpiperazine- 1-carbonyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 132

8-hydroxy-9-(4-((4-methylpiperazin- 1-yl)methyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 133

8-methoxy-9-(4-((4-methylpiperazin- 1-yl)methyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 134

(E)-9-(3-(diethylamino)prop-1-enyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 135

(E)-9-(3-(4-(aminomethyl)piperidin-1- yl)prop-1-enyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 136

(E)-9-(3-(2-(diethylamino)ethyl amino)prop-1-enyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 137

N-(4-(8-hydroxy-4-oxo-2,3,4,5-tetra hydro-1H-cyclopenta[c]quinolin- 9-yl)phenyl)methanesulfonamide 138

9-(2-(dimethylamino)pyrimidin-5-yl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 139

tert-butyl (1-(methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzyl)piperidin-4-yl)methyl carbamate 140

8-hydroxy-9-(4-(4-methylpiperazin-1- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one 141

8-methoxy-9-(4-(4-methylpiperazin-1- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one diydrochloride 142

8-methoxy-9-(1-(methylsulfonyl)-1,2, 3,6-tetrahydropyridin-4-yl)thieno [2,3-c]quinolin-4(5H)-one 143

(E)-9-(3-(diethylamino)prop-1-enyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 144

9-(3-(4-(aminomethyl)piperidin-1-yl) propyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 145

9-(4-(3-(2-(diethylamino)ethylamino) propoxy)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 146

9-(4-(3-diethylamino)propoxy) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 147

9-(4-(3-(2-(diethylamino)ethylamino) propoxy)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 148

(E)-9-(3-(4-(aminomethyl)piperidin-1- yl)prop-1-enyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 149

9-(4-(3-(dimethylamino)propoxy) phenyl)-8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 150

8-hydroxy-9-(4-(2-(piperidin-1-yl) ethoxy)phenyl)thieno[2,3-c] quinolin-4(5H)-one 151

9-(4-(2-(ethylamino)ethoxy)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 152

(E)-9-(3-(4-aminopiperidin-1-yl) prop-1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 153

9-(1-(2-aminoethyl)-1,2,3,6-tetra hydropyridin-4-yl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 154

9-(4-(2-(ethylamino)ethoxy)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 155

9-(4-(2-(diethylamino)ethoxy)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 156

9-(4-(2-(diethylamino)ethoxy)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 157

9-(4-(2-(dimethylamino)ethoxy) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 158

9-(4-(2-(dimethylamino)ethoxy) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 159

8-methoxy-9-(4-(2-(piperidin-1-yl) ethoxy)phenyl)thieno[2,3-c] quinolin-4(5H)-one 160

8-methoxy-9-(3-(2-(4-methyl piperazin-1-yl)ethoxy)phenyl) thieno[2,3-c]quinolin-4(5H)-one 161

9-(3-(2-(diethylamino)ethoxy)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 162

9-(3-(3-(diethylamino)propoxy)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 163

9-(4-(2-(dimethylamino)ethyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 164

9-(4-((dimethylamino)methyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 165

9-(4-((dimethylamino)methyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 166

9-(3-(2-(diethylamino)ethoxy)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 167

8-hydroxy-9-(3-(2-(4-methylpiperazin- 1-yl)ethoxy)phenyl)thieno[2,3-c] quinolin-4(5H)-one 168

N-ethyl-N-(2-(4-(8-methoxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) phenylmethoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenoxy) ethyl)methanesulfonamide 169

9-(4-(2-aminoethyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 170

2-(3-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) acetonitrile 171

2-(3-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) acetonitrile 172

9-(1-(2-(dimethylamino)ethyl)-1,2,3, 6-tetrahydropyridin-4-yl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 173

N-(hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) methanesulfonamide 174

9-(1-(2-(diethylamino)ethyl)-1,2,3,6- tetrahydropyridin-4-yl)-8-hydroxy thieno[2,3-c]quinolin- 4(5H)-one 175

9-(4-(2-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 176

9-(4-(2-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 177

N-(methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) methanesulfonamide 178

N-(methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenethyl) methanesulfonamide 179

N-(2-aminoethyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide hydrochloride 180

8-hydroxy-9-(1,2,3,6-tetrahydro pyridin-4-yl)-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one hydrochloride 181

9-(4-(1-(dimethylamino)ethyl)phenyl)- 8-hydroxy-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one hydrochloride 182

9-(4-(2-(dimethylamino)ethyl)phenyl)- 8-methoxy-2,3-dihydro-1H-cyclo penta[c]quinolin-4(5H)-one 183

9-(4-((diethylamino)methyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 184

9-(4-((diethylamino)methyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 185

9-(3-(2-(dimethylamino)ethyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 186

9-(3-(2-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one 187

8-hydroxy-9-(4-((methylamino) methyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one 188

8-methoxy-9-(4-((methylamino) methyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one 189

9-(4-amino-3-methoxyphenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 190

3-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzonitrile 191

9-(4-(1-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 192

9-(4-(1-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 193

N-(1-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethyl)methanesulfonamide 194

8-hydroxy-9-(4-(1-(pyrrolidin-1-yl) ethyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 195

9-(4-(1-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 196

9-(4-(1-(diethylamino)ethyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 197

N-(2-aminoethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide hydrochloride 198

N-(2-(dimethylamino)ethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide hydrochloride 199

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)- N-(pyrrolidin-3-yl)benzenesulfonamide hydrochloride 200

N-(azetidin-3-yl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide hydrochloride 201

9-(4-(2-(diethylamino)ethyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 202

2-amino-N-(3-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethanesulfonamide hydrochloride 203

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzonitrile 204

4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzonitrile 205

(E)-9-(3-(3-aminopyrrolidin-1-yl) prop-1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride 206

N-(2-hydroxyethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide 207

8-methoxy-9-(5-methoxypyridin-3- yl)thieno[2,3-c]quinolin-4(5H)-one hydrochloride 208

N-methoxy-9-(5-methoxypyridin-3- yl)-2,3-dihydro-1H-cyclopenta[c] quinolin-4(5H)-one hydrochloride 209

9-(4-(3-aminopyrrolidin-1-ylsulfonyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 210

N-(2-bromoethyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide 211

9-(4-((diisopropylamino)methyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 212

N-(hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)benzyl)methane sulfonamide 213

9-(4-((isopropylamino)methyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 214

2-(dimethylamino)-N-(3-(8-hydroxy- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)ethane sulfonamide hydrochloride 215

2-amino-N-(3-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethanesulfonamide hydrochloride 216

8-methoxy-9-(4-(1-(pyrrolidin-1-yl) ethyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 217

9-(4-amino-3-hydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 218

N-(2-methoxy-4-(8-methoxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) phenyl)methanesulfonamide 219

9-(3,5-difluoro-4-hydroxyphenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 220

N-(2-hydroxy-4-(8-hydroxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) phenyl)methanesulfonamide 221

9-(4-((4-(aminomethyl)piperidin-1- yl)methyl)-3-fluorophenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one dihydrochloride 222

9-(4-(2-(dimethylamino)ethyl)phenyl)- 6-fluoro-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 223

9-(3,5-difluoro-4-hydroxyphenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 224

6-fluoro-8-methoxy-9-(1,2,3,6-tetra hydropyridin-4-yl)thieno[2,3-c] quinolin-4(5H)-one hydrochloride 225

9-(4-(1-(dimethylamino)ethyl)phenyl)- 6-fluoro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 226

9-(4-((diethylamino)methyl)-3-fluoro phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 227

(E)-9-(3-(3-hydroxypyrrolidin-1-yl) prop-1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 228

(E)-8-hydroxy-9-(3-(3-hydroxy pyrrolidin-1-yl)prop-1-enyl)thieno [2,3-c]quinolin-4(5H)-one 229

8-hydroxy-9-(4-((isopropylamino) methyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 230

(E)-9-(3-(3-aminoazetidin-1-yl) prop-1-enyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride 231

(E)-8-methoxy-9-(3-(2-(methyl sulfonyl)ethylamino)prop-1-enyl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride 232

(S)-9-(4-(1-aminoethyl)phenyl)-8- methoxythieno[2,3-c]quinolin-4(5H)- one hydrochloride 233

(S)-9-(4-(1-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride 234

8-hydroxy-9-(5-hydroxypyridin-3-yl)- 2,3-dihydro-1H-cyclopenta[c] quinolin-4(5H)-one hydrochloride 235

9-(4-((4-(aminomethyl)piperidin-1-yl) methyl)-3-fluorophenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one 236

8-methoxy-9-(4-(1-(2-(methyl sulfonyl)ethylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride 237

9-(4-((3-aminopyrrolidin-1-yl)methyl)- 3-fluorophenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one dihydrochloride 238

(E)-9-(3-(3-aminoazetidin-1-yl) prop-1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride 239

(E)-9-(3-(ethylamino)prop-1-enyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride 240

9-(4-((3-aminopiperidin-1-yl)methyl)- 3-fluorophenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one dihydrochloride 241

9-(4-((3-aminopyrrolidin-1-yl)methyl)- 3-fluorophenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one dihydrochloride 242

9-(4-((3-aminopiperidin-1-yl)methyl)- 3-fluorophenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one dihydrochloride 243

8-hydroxy-9-(4-(1-(2-(methylsulfonyl) ethylamino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 244

(E)-9-(3-(3-aminopiperidin-1-yl)prop- 1-enyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride 245

(E)-9-(3-(3-aminopyrrolidin-1-yl) prop-1-enyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride 246

(E)-9-(3-(3-aminopiperidin-1-yl)prop- 1-enyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride 247

(E)-8-hydroxy-9-(3-(2-(methyl sulfonyl)ethylamino)prop-1-enyl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride 248

8-methoxy-9-(4-(2-(2-(methyl sulfonyl)ethylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride 249

2-(2-fluoro-4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)acetonitrile 250

(E)-N-(1-(3-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)allyl) azetidin-3-yl)methanesulfonamide hydrochloride 251

4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N,N- dimethylbenzenesulfonamide 252

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-methyl benzenesulfonamide 253

tert-butyl (5-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)furan-2-yl) methylcarbamate 254

N-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-2-methyl phenyl)methanesulfonamide 255

N-(4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-2-methyl phenyl)methanesulfonamide 256

9-(4-(aminomethyl)phenyl)-6-fluoro- 8-hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride 257

9-(4-(aminomethyl)phenyl)-6-fluoro- 8-methoxythieno[2,3-c]quinolin-4(5H)- one hydrochloride 258

6-fluoro-8-hydroxy-9-(1,2,3,6-tetra hydropyridin-4-yl)thieno[2,3-c] quinolin-4(5H)-one 259

9-(4-((diethylamino)methyl)-3-fluoro phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 260

8-methoxy-9-(4-(1-(piperidin-1-yl) ethyl(phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 261

2-(2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)acetonitrile 262

8-hydroxy-9-(4-(1-(piperidin-1-yl) ethyl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 263

(E)-9-(3-(3-(dimethylamino)piperidin- 1-yl)prop-1-enyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one dihydrochloride 264

(E)-9-(3-(3-(dimethylamino) pyrrolidin-1-yl)prop-1-enyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one dihydrochloride 265

9-(4-(2-aminoethyl)-3-fluorophenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 266

9-(5-(aminomethyl)thiophen-2-yl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 267

9-(4-((ethylamino)methyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 268

(E)-9-(3-(4-aminopiperidin-1-yl) prop-1-enyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride 269

9-(4-((ethylamino)methyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 270

9-(4-(aminomethyl)phenyl)-6-bromo- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 271

9-(3-chloro-4-((diethylamino)methyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 272

(R)-9-(4-(1-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 273

9-(4-(3-aminopropyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 274

(R)-9-(4-(1-aminoethyl)phenyl)-8- methoxythieno[2,3-c]quinolin-4(5H)- one hydrochloride 275

(R)-9-(4-(1-aminoethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride 276

9-(4-(2-aminoethyl)-3-fluorophenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 277

9-(4-(1-amino-2-methylpropan-2-yl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 278

9-(3-fluoro-4-((3-hydroxypyrrolidin- 1-yl)methyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one hydrochloride 279

9-(3-fluoro-4-((3-hydroxypyrrolidin- 1-yl)methyl)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one hydrochloride 280

4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2,2,2- trifluoroethyl)benzenesulfonamide 281

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2,2,2- trifluoroethyl)benzenesulfonamide 282

N-(2-(dimethylamino)ethyl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)benzenesulfonamide 283

8-hydroxy-9-(4-((2-(methylsulfonyl) ethylamino)methyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one 284

9-(3-(3-(dimethylamino)pyrrolidin-1- yl)propyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride 285

9-(1-(2-aminoethyl)-1H-pyrazol-4-yl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one dihydrochloride 286

9-(3-chloro-4-((diethylamino)methyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride hydrochloride 287

4-(7-fluoro-8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)-N-(2- hydroxyethyl)benzenesulfonamide 288

9-(3-acetylphenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 289

2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)- N-(2-hydroxyethyl)benzamide 290

3-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) propanenitrile 291

9-(4-acetylphenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 292

2-fluoro-N-(2-hydroxyethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)benzamide 293

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2- hydroxyethyl)benzamide 294

1,1-diethyl-3-(hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzyl)urea 295

N-(2-hydroxyethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzamide 296

9-(4-acetylphenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 297

N-(2-bromoethyl)-2-fluoro-4-(8- hydroxy-4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)benzenesulfonamide 298

9-(3-(3-(dimethylamino)piperidin-1- yl)propyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one dihydrochloride 299

N-(2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenethyl)methanesulfonamide 300

9-(3-fluoro-4-(2-(methylsulfonamido) ethyl)phenyl)-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-8-yl methanesulfonate 301

(R)-N-(1-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethyl)methanesulfonamide 302

(R)-9-(4-(1-(methylsulfonamido) ethyl)phenyl)-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-8-yl methanesulfonate 303

2-fluoro-N-(2-hydroxyethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)benzene sulfonamide 304

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N,N- dimethylbenzenesulfonamide 305

9-(4-(2-(dimethylamino)ethyl)phenyl)- 7-fluoro-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 306

N-(2-bromoethyl)-4-(7-fluoro-8- hydroxy-4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)benzenesulfonamide 307

4-(7-fluoro-8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)-N- (2-hydroxy ethyl)benzene sulfonamide 308

9-(4-(1-(dimethylamino)-2- methylpropan-2-yl)phenyl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one hydrochloride 309

N-(2-chloro-4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzyl)-N-methylmethane sulfonamide 310

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2- methoxyethyl)benzenesulfonamide 311

(E)-3-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-2-methyl acrylonitrile 312

N-(2-fluoro-4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenethyl)methanesulfonamide 313

8-hydroxy-9-(4-(1-hydroxyethyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 314

9-(4-(1-(cyclopentylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 315

9-(4-(1-(cyclopentylamino)ethyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 316

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(2- hydroxyethyl)benzenesulfonamide 317

9-(5-(aminomethyl)furan-2-yl)-8- hydroxythieno[2,3-c]quinolin-4(5H)- one hydrochloride 318

9-(3-chloro-4-((methylamino)methyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 319

9-(4-(2-aminopropan-2-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 320

N-(3-hydroxypropyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide 321

2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)-N- (2-hydroxyethyl)benzenesulfonamide 322

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(3- hydroxypropyl)benzenesulfonamide 323

N-(3-bromopropyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide 324

2-fluoro-4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl)-N- (2-methoxyethyl)benzenesulfonamide 325

9-(3-chloro-4-((methylamino)methyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 326

9-(4-(aminomethyl)phenyl)-4-oxo-4,5- dihydrothieno[2,3-c]quinoline-8- carbonitrile hydrochloride 327

9-(4-(2-(dimethylamino)ethyl)-3- fluorophenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 328

9-(4-(aminomethyl)phenyl)-6,7- dichloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 329

9-(4-(aminomethyl)phenyl)-6-chloro- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 330

9-(4-(aminomethyl)phenyl)-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-8-yl trifluoromethanesulfonate hydrochloride 331

9-(4-(2-(dimethylamino)ethyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 332

N-(2-chloroethyl)-4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide 333

N-(2-fluoroethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide 334

9-(4-(2-aminopropan-2-yl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 335

(S)-9-(4-(1-(dimethylamino)ethyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 336

9-(4-(1-aminopropyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 337

9-(4-(1-aminopropyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 338

9-(4-(1-(diethylamino)propyl)phenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 339

9-(4-(1-(dimethylamino)propyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 340

9-amino-8-methoxythieno[2,3-c] quinolin-4(5H)-one 341

9-(4-(1-(dimethylamino)ethyl)phenyl)- 6,7-difluoro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 342

9-(4-(1-(dimethylamino)ethyl)phenyl)- 6,7-difluoro-8-methoxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 343

N-cyclopropyl-4-(8-methoxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) benzenesulfonamide 344

N-cyclopropyl-4-(8-hydroxy-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin-9-yl) benzenesulfonamide 345

9-(2-amino-2,3-dihydro-1H-inden-5- yl)-8-hydroxythieno[2,3-c]quinolin-4 (5H)-one hydrochloride 346

9-(4-(1-(dimethylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 347

(S)-N-(1-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethyl)methanesulfonamide 348

9-(4-(1-(aminomethyl)cyclopropyl) phenyl)-8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 349

9-(4-(1-(dimethylamino)ethyl)-3- fluorophenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 350

N-(1-(hydroxymethyl)cyclopentyl)-4- (8-methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)benzene sulfonamide 351

9-(2-(diethylamino)-2,3-dihydro-1H- inden-5-yl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 352

9-(2-(dimethylamino)-2,3-dihydro-1H- inden-5-yl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 353

8-hydroxy-9-(1,2,3,4-tetrahydroiso quinolin-7-yl)thieno[2,3-c]quinolin-4 (5H)-one hydrochloride 354

8-methoxy-9-(1,2,3,4-tetrahydroiso quinolin-7-yl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 355

3-(3-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) propanenitrile 356

9-(4-(1-(diethylamino)ethyl)-3-fluoro phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 357

1-(4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) cyclopropanecarbonitrile 358

9-(2-ethyl-1,2,3,4-tetrahydroiso quinolin-7-yl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 359

9-(4-(1-aminoethyl)-3-fluorophenyl)- 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 360

3-(3-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) propanenitrile 361

1-(4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl) cyclopropanecarbonitrile 362

9-(2-amino-2,3-dihydro-1H-inden-5- yl)-8-methoxythieno[2,3-c]quinolin-4 (5H)-one hydrochloride 363

N-isopentyl-4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzenesulfonamide 364

9-(2-(dimethylamino)-2,3-dihydro-1H- inden-5-yl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 365

9-(4-(1-(ethylamino)ethyl)phenyl)-8- methoxythieno[2,3-c]quinolin-4(5H)- one hydrochloride 366

6-chloro-9-(4-(1-(dimethylamino) ethyl)phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one hydrochloride 367

9-(4-(cyclopropanecarbonyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 368

9-(4-(aminomethyl)phenyl)-4-oxo-4,5- dihydrothieno[2,3-c]quinoline-8- carboxamide hydrochloride 369

9-(2-aminoethyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one 370

8-hydroxy-9-(4-(2-hydroxyethylsulfonyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 371

9-(4-(2-hydroxyethylsulfonyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 372

9-(1-ethylindolin-5-yl)-8-hydroxy thieno[2,3-c]quinolin-4(5H)-one hydrochloride 373

9-(4-(1-aminopropan-2-yl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 374

8-hydroxy-9-(2-methyl-1,2,3,4-tetra hydroisoquinolin-7-yl)thieno[2,3-c] quinolin-4(5H)-one hydrochloride 375

9-(4-(1-aminoethyl)-3-fluorophenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 376

8-hydroxy-9-(1-methylindolin-5-yl) thieno[2,3-c]quinolin-4(5H)-one hydrochloride 377

8-hydroxy-9-(indolin-5-yl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 378

9-(indolin-5-yl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 379

9-(4-(1-((dimethylamino)methyl) cyclopropyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one hydrochloride 380

4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-propyl benzenesulfonamide 381

N-(cyclopropylmethyl)-4-(8-methoxy- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide 382

N-(3,3-dimethylbutyl)-4-(8-methoxy- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide 383

4-(8-hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)-N-isopentyl benzenesulfonamide 384

N-(3,3-dimethylbutyl)-4-(8-hydroxy- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide 385

9-(4-(1-(ethylamino)ethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 386

3-(4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)phenyl)-3- oxopropanenitrile 387

(E)-9-(2-ethoxyvinyl)-8-methoxy thieno[2,3-c]quinolin-4(5H)-one 388

N-(1-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)phenyl)ethyl)acetamide 389

4-(8-methoxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(3,3,3- trifluoropropyl)benzenesulfonamide 390

4-(8-hydroxy-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl)-N-(1- (hydroxymethyl)cyclopentyl) benzenesulfonamide 391

N-(2,2-difluoroethyl)-4-(8-methoxy-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)benzenesulfonamide (Examples 1031-1438) No. Molecule Name 1031

8-methoxy-9-(4-(1-methoxyethyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1032

9-(4-(1-aminoethyl)phenyl)-6- bromo-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1033

8-methoxy-9-(2-((piperidin-3- ylmethyl)amino)ethyl)thieno[2,3- c]quinolin-4(5H)-one 1034

9-(2-(4-((dimethylamino)methyl) piperidin-1-yl)ethyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1035

tert-butyl 4-((2-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)ethyl)amino)piperidine-1- carboxylate 1036

8-methoxy-9-(2-(piperidin-4-yl amino)ethyl)thieno[2,3-c] quinolin-4(5H)-one 1037

4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)-N-(3,33-trifluoropropyl) benzenesulfonamide 1038

3H-pyrrolo[2,3-c]quinolin- 4(5H)-one 1039

9-(4-(1-aminoethyl)phenyl)-6- cyclopropyl-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1040

9-(4-(1-aminoethyl)phenyl)-8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinoline-6-carbonitrile 1041

9-(4-(1-aminoethyl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1042

8-hydroxy-9-(2-(4-((methylamino) methyl)piperidin-1-yl)ethyl) thieno[2,3-c]quinolin-4(5H)-one 1043

8-methoxy-9-(2-(4-((methylamino) methyl)piperidin-1-yl)ethyl) thieno[2,3-c]quinolin-4(5H)-one 1044

9-(2-(4-((dimethylamino)methyl) piperidin-1-yl)ethyl)-8- hydroxythieno[2,3-c] quinolin-4(5H)-one 1045

9-(4-(1-hydroxypropyl)phenyl)- 8-methoxythieno[2,3-c] quinolin-4(5H)-one 1046

(R)-8-methoxy-9-(4-(1-(methyl amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one 1047

(R)-8-(4-(1-aminoethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1048

(R)-tert-butyl (1-(4-(4-oxo-4,5-dihydrothieno [2,3-c]quinolin-8-yl)phenyl) ethyl)carbamate 1049

9-(4-(4-hydroxypiperidin-4-yl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one 1050

(R)-8-(4-(1-(dimethylamino) ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one 1051

8-hydroxy-9-(4-(1,2,3,6- tetrahydropyridin-4-yl) phenyl)thieno[2,3-c] quinolin-4(5H)-one 1052

(R)-8-hydroxy-9-(4-(1-(methyl amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one 1053

8-hydroxy-9-(4-(1- hydroxypropyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one 1054

(R)-8-hydroxy-9-(4-(1-hydroxy ethyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 1055

8-hydroxy-9-(4-(4- hydroxypiperidin-4- yl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 1056

(S)-8-hydroxy-9-(4-(1-hydroxy ethyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 1057

N-(1-hydroxypropan-2-yl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide 1058

9-(4-(hydroxy(thiazol-2-yl) methyl)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1059

9-(6-(1-aminoethyl)pyridin-3- yl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1060

9-(4-(4-hydroxybutyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1061

2-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)phenyl)-2-methylpropanamide 1062

N-(1-bromopropan-2-yl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide 1063

8-hydroxy-9-(4-(hydroxy (thiazol-2-yl)methyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1064

(S)-8-methoxy-9-(4-(1-(methyl amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one 1065

9-(6-(1-(diethylamino)ethyl) pyridin-3-yl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1066

9-(4-(1-aminoethyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1067

9-(6-(1-aminoethyl)pyridin-3- yl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 1068

8-hydroxy-9-(4-(4-hydroxybutyl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1069

9-(4-(3-amino-1-hydroxypropyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one 1070

9-(6-(1-(dimethylamino)ethyl) pyridin-3-yl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1071

9-(6-(1-(dimethylamino)ethyl) pyridin-3-yl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1072

4-((4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)-1H-pyrazol-1-yl)methyl) benzonitrile 1073

8-aminothieno[2,3-c]quinolin- 4(5H)-one 1074

9-(4-((1H-pyrazol-1-yl)methyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one 1075

9-(6-(1-aminoethyl)pyridin-3- yl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 1076

9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl dimethylcarbamate 1077

9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl isopropyl carbonate 1078

9-(4-((1H-imidazol-1-yl)methyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one 1079

N-(2-bromopropyl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide 1080

(R)-9-(4-(1-aminoethyl)phenyl)- 6,7-dichloro-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1081

(R)-9-(4-(1-aminoethyl)phenyl)- 6-chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1082

(S)-8-hydroxy-9-(4-(1- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin- 4(5H)-one 1083

9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl diethylcarbamate 1084

4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)-N-(2-hydroxyethyl)- N-methylbenzenesulfonamide 1085

N-(2-hydroxyethyl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)-N- methylbenzenesulfonamide 1086

9-(4-((1H-pyrazol-1-yl(methyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1087

(S)-6-chloro-8-hydroxy-9-(4-(1- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1088

9-(4-(1-aminopropyl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1089

9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl morpholine-4-carboxylate 1090

N-(2-hydroxyethyl)-4-(8- methoxy-4-oxo-2,3,4,5- tetrahydro-1H-cyclopenta [c]quinolin-9-yl) benzenesulfonamide 1091

8-bromothieno[2,3-c]quinolin- 4(5H)-one 1092

9-(4-(2-(dimethylamino)propyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1093

9-(4-(2-aminopropyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1094

N-(2-bromoethyl)-4-(8-hydroxy- 4-oxo-2,3,4,5-tetrahydro-1H- cyclopenta[c]quinolin-9-yl) benzenesulfonamide 1095

9-(4-(2-aminopropyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1096

8-methoxy-9-(1-(2-morpholino ethyl)-1H-pyrazol-4-yl)thieno [2,3-c]quinolin-4(5H)-one 1097

9-(4-(2-(diethylamino)propyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1098

9-(4-(1-aminoethyl)phenyl)-8- hydroxy-6-(hydroxymethyl) thieno[2,3-c]quinolin-4(5H)-one 1099

9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-8-yl acetate 1100

9-(1-(1-(dimethylamino)propan- 2-yl)-1H-pyrazol-4-yl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1101

9-(4-((1H-imidazol-1-yl)methyl) phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1102

9-(4-(aminomethyl)phenyl)-8- (2-morpholinoethoxy)thieno[2,3- c]quinolin-4(5H)-one 1103

8-hydroxy-9-(1-(2- morpholinoethyl)-1H-pyrazol- 4-yl)thieno[2,3-c]quinolin- 4(5H)-one 1104

N-(2-(1H-pyrazol-1-yl)ethyl)- 4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)benzenesulfonamide 1105

8-hydroxy-9-(4-(2,2,2-trifluoro- 1-hydroxyethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one 1106

9-(4-(2-aminopropyl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1107

N-(2-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9- yl)phenyl)-2-methylpropyl) methanesulfonamide 1108

9-(4-(2-(dimethylamino)propyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one 1109

9-(4-(1-aminoethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1110

9-(1-(1-(dimethylamino)propan- 2-yl)-1H-pyrazol-4-yl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1111

9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1112

9-(4-(1-(dimethylamino)propan- 2-yl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1113

8-methoxy-9-(4-(2,2,2-trifluoro- 1-hydroxyethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one 1114

N-(2-bromoethyl)-4-(8-hydroxy- 4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)-N- methylbenzenesulfonamide 1115

N-(2-(1H-imidazol-1-yl)ethyl)- 4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) benzenesulfonamide 1116

9-(4-(1-(aminomethyl) cyclopropyl)phenyl)-6-chloro-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1117

3-(4-(8-(2-(dimethylamino) ethoxy)-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl) propanenitrile 1118

(R)-9-(4-(1-aminopropyl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 1119

N-(2-chloroethyl)-4-(8-hydroxy- 4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)-N- methylbenzenesulfonamide 1120

(S)-9-(4-(1-aminopropyl) phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1121

(S)-9-(4-(1-aminopropyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one 1122

(R)-9-(4-(1-aminoethyl)phenyl)- 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1123

(R)-9-(4-(1-aminoethyl)phenyl)- 6-bromo-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1124

9-(4-(1-aminoethyl)phenyl)-4- oxo-4,5-dihydrothieno[2,3-c] quinoline-8-carbonitrile 1125

9-(4-(1-aminoethyl)phenyl)-8- (hydroxymethyl)thieno[2,3-c] quinolin-4(5H)-one 1126

(R)-6-chloro-9-(4-(1- (dimethylamino)ethyl)phenyl)- 8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1127

(S)-9-(4-(1-(ethylamino)propyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1128

(S)-9-(4-(1-(dimethylamino) propyl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1129

6-chloro-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1130

9-(4-(1-aminoethyl)phenyl)-6- ethynyl-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1131

(R)-9-(4-(1-aminopropyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1132

(R)-6-chloro-8-hydroxy-9-(4-(1- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1133

9-(4-(2-aminoethyl)phenyl)-6- chloro-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1134

9-(4-(1-aminoethyl)phenyl)-8- (difluoromethyl)thieno[2,3-c] quinolin-4(5H)-one 1135

(R)-6-bromo-8-hydroxy-9-(4- (1-(methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1136

9-(4-(1-aminopropan-2-yl) phenyl)-6-chloro-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1137

9-(4-butylphenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1138

9-(4-butylphenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1139

N-(2-chloroethyl)-4-(8-methoxy- 4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl) benzenesulfonamide 1140

9-(4-((3-bromopyrrolidin-1-yl) sulfonyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1141

(S)-9-(4-(1-(methylsulfonamido) propyl)phenyl)-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate 1142

9-(4-(2-aminoethyl)phenyl)-6- bromo-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1143

9-(4-(3-(dimethylamino)-1- hydroxypropyl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1144

N-(2-bromoethyl)-4-(6-chloro- 8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide 1145

N-(2-chloroethyl)-4-(8-hydroxy- 4-oxo-2,3,4,5-tetrahydro-1H- cyclopenta[c]quinolin-9-yl) benzenesulfonamide 1146

N-(2-bromoethyl)-4-(5-ethyl-8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide 1147

(S)-8-methoxy-9-(4-(1-(methyl amino)propyl)phenyl)thieno[2, 3-c]quinolin-4(5H)-one 1148

(S)-8-hydroxy-9-(4-(1- (methylamino)propyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1149

9-(4-(1-aminoethyl)phenyl)-8- (((2-hydroxyethyl)amino)methyl) thieno[2,3-c]quinolin-4(5H)- one 1150

(R)-9-(4-(1-aminopropyl)phenyl)- 6-bromo-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1151

(R)-9-(4-(1-(dimethylamino) propyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1152

8-hydroxy-9-(4-pentylphenyl) thieno[2,3-c]quinolin-4(5H)-one 1153

9-(4-(2-aminoacetyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1154

(S)-6-chloro-8-hydroxy-9-(4-(1- (methylamino)propyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1155

8-hydroxy-9-(4-(2-(methylamino) ethyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 1156

8-methoxy-9-(4-(2-(methylamino) ethyl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 1157

(R)-9-(4-(1-aminopropyl)phenyl)- 8-hydroxy-6-methylthieno[2, 3-c]quinolin-4(5H)-one 1158

(R)-9-(4-(1-aminopropyl)phenyl)- 8-methoxy-6-methylthieno[2, 3-c]quinolin-4(5H)-one 1159

(R)-9-(4-(1-aminopropyl)phenyl)- 6-chloro-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1160

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1161

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 1162

2-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)butanenitrile 1163

(S)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1164

(S)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 1165

6-chloro-8-hydroxy-9-(4-(2- (methylamino)ethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one 1166

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-6-chloro-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1167

9-(4-(2-aminoethyl)-3,5- difluorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1168

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1169

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1170

6-chloro-8-methoxy-9-(4-(2- (methylamino)ethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one 1171

9-(4-(2-aminoethyl)-3- chlorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1172

(S)-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1173

6-bromo-8-methoxy-9-(4-(2- (methylamino)ethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one 1174

9-(4-(1-aminopropan-2-yl)-3- fluorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1175

(R)-9-(4-(1-aminopropyl)phenyl)- 6-chloro-8-methoxythieno[2, 3-c]quinolin-4(5H)-one 1176

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-6-bromo-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1177

9-(4-(2-aminoethyl)-3,5- difluorophenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1178

9-(4-(2-(dimethylamino)ethyl)- 3,5-difluorophenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1179

9-(4-(1-aminopropan-2-yl)-3- fluorophenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1180

(S)-9-(4-(1-aminopropan-2-yl) phenyl)-6,7-dichloro-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1181

(S)-9-(4-(1-aminopropan-2-yl) phenyl)-6-chloro-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1182

(S)-6-chloro-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1183

6-bromo-8-hydroxy-9-(4-(2- (methylamino)ethyl)phenyl)thieno [2,3-c]quinolin-4(5H)-one 1185

N-(2-hydroxyethyl)-4-(8-methoxy- 5-methyl-4-oxo-4,5-dihydro thieno[2,3-c]quinolin-9-yl) benzenesulfonamide 1186

methyl 3-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)propanoate 1187

(R)-8-hydroxy-9-(4-(1-(methyl amino)propan-2-yl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1188

(R)-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1189

(R)-8-methoxy-9-(4-(1-(methyl amino)propan-2-yl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1190

9-(4-(1-aminopropan-2-yl)-3- fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1191

9-(4-(2-aminoethyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1192

9-(4-(2-aminoethyl)phenyl)-8- methoxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1193

9-(4-(1-(dimethylamino)propan- 2-yl)-3-fluorophenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1194

(S)-6-chloro-8-hydroxy-9-(4-(1- (methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1195

(S)-6-chloro-9-(4-(1-(diethylamino) propan-2-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1196

(S)-8-methoxy-9-(4-(1-(methyl amino)propan-2-yl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1197

(S)-8-hydroxy-9-(4-(1- (methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1198

4-(8-hydroxy-5-methyl-4-oxo-4, 5-dihydrothieno[2,3-c]quinolin- 9-yl)-N-(2-hydroxyethyl) benzenesulfonamide 1199

N-(2-bromoethyl)-4-(8-hydroxy- 5-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide 1200

(R)-6-chloro-9-(4-(1-(dimethyl amino)propan-2-yl)phenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1201

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-6-chloro-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1202

9-(4-(1-aminobutan-2-yl)phenyl)- 8-methoxythieno[2,3-c] quinolin-4(5H)-one 1203

9-(4-(2-aminopropan-2-yl) phenyl)-8-hydroxy-2-(phenylsulfonyl) thieno[2,3-c]quinolin-4(5H)-one 1204

N-(1-chloropropan-2-yl)-4-(8- hydroxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide 1205

N-(1-chloropropan-2-yl)-4-(8- methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) benzenesulfonamide 1206

9-(4-(2-aminoethyl)-3-hydroxy phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1207

9-(4-(2-aminoethyl)-3-methoxy phenyl)-8-methoxythieno[2,3-c] quinolin-4(5H)-one 1208

9-(4-(2-aminoethyl)-2-chloro-5- methoxyphenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1209

9-(4-(3-(aminomethyl)pentan- 3-yl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1210

(R)-9-(4-(1-aminopropy)phenyl)- 8-hydroxy-5,6-dimethylthieno [2,3-c]quinolin-4(5H)-one 1211

9-(4-(2-aminoethyl)-2-chloro-5- hydroxyphenyl)-6-chloro-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1212

9-(4-(aminomethyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1213

9-(4-(2-aminoethyl)-3- fluorophenyl)-6-bromo-8- hydroxythieno[2,3-c] quinolin-4(5H)-one 1214

9-(4-(2-aminoethyl)-3- fluorophenyl)-6-bromo- 8-methoxythieno [2,3-c]quinolin-4(5H)-one 1215

(S)-8-hydroxy-6-methyl-9-(4-(1- (methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1216

9-(4-(2-aminoethyl)-3- fluorophenyl)-8-methoxy- 6-methylthieno[2,3-c] quinolin-4(5H)-one 1217

9-(4-(2-aminoethyl)-3- fluorophenyl)-8-hydroxy- 6-methylthieno [2,3-c]quinolin-4(5H)-one 1218

9-(4-(2-aminoethyl)-3- fluorophenyl)-6-chloro- 8-methoxythieno [2,3-c]quinolin-4(5H)-one 1219

9-(4-(2-aminoethyl)-3- fluorophenyl)-6-chloro-8- hydroxythieno[2,3-c] quinolin-4(5H)-one 1220

9-(4-(2-aminoethyl)-3-fluorophenyl)- 6-cyclopropyl-8-methoxy thieno[2,3-c]quinolin-4(5H)-one 1221

9-(4-(2-aminoethyl)-3- fluorophenyl)-6-cyclopropyl- 8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1222

(S)-8-methoxy-6-methyl-9-(4- (1-(methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1223

(S)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1224

9-(4-(2-aminoethyl)-2-bromo-5- hydroxyphenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1225

(S)-9-(4-(1-aminoethyl)phenyl)- 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1226

3-(4-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propanenitrile 1227

9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin-4(5H)- one 1228

9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin-4(5H)- one 1229

2-(2-fluoro-4-(8-hydroxy-6- methyl-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl) propanenitrile 1230

6-cyclopropyl-9-(4-(2- (dimethylamino)ethyl)-3- fluorophenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1231

6-cyclopropyl-9-(4-(2- (dimethylamino)ethyl)-3- fluorophenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1232

(S)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1233

(S)-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1234

9-(3-fluoro-4-(2-(methylamino) ethyl)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1235

9-(3-fluoro-4-(2-(methylamino) ethyl)phenyl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1236

9-(4-(2-amino-1-cyclopentylethyl) phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1237

9-(4-(2-amino-1,1- dicyclopentylethyl)phenyl)- 8-methoxythieno [2,3-c]quinolin-4(5H)-one 1238

3-(4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propanenitrile 1239

9-(4-(2-amino-1-cyclopentylethyl) phenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one 1240

9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-cyclopropyl-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1241

9-(4-(3-aminopropyl)phenyl)-8- methoxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1242

9-(4-(2-aminopropyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1243

9-(4-(2-aminopropyl)phenyl)-8- methoxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1244

9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-cyclopropyl-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1245

6-bromo-9-(3-fluoro-4-(2- (methylamino)ethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1246

6-bromo-9-(3-fluoro-4-(2- (methylamino)ethyl)phenyl)- 8-methoxythieno[2,3-c]quinolin- 4(5H)-one 1247

9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-bromo-8-hydroxy thieno[2,3-c]quinolin-4(5H)- one 1248

9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-bromo-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1249

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-6-methyl-4-oxo-4,5- dihydrothieno[2,3-c]quinoline- 8-carbonitrile 1250

(R)-9-(4-(1-aminoethyl)phenyl)- 8-hydroxy-6-vinylthieno[2,3- c]quinolin-4(5H)-one 1251

9-(4-(1-(aminomethyl) cyclopropyl)phenyl)-8-methoxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1252

9-(4-(1-amino-3-methylbutan-2- yl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1253

9-(4-(1-amino-3-methylbutan-2- yl)phenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one 1254

9-(4-(1-(aminomethyl) cyclopropyl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1255

(R)-9-(4-(1-aminoethyl)phenyl)- 6-ethyl-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1256

(R)-9-(4-(1-aminoethyl)phenyl)- 6-(difluoromethyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1257

9-(3-fluoro-4-(2-(methylamino) ethyl)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1258

9-(3-fluoro-4-(2-(methylamino) ethyl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1259

6-bromo-9-(4-(1-(dimethylamino)- 2-methylpropan-2-yl)phenyl)- 8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1260

9-(4-(1-amino-2-methylpropan- 2-yl)phenyl)-6-chloro-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1261

9-(4-(3-aminopropyl)phenyl)-8- hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1262

(R)-8-hydroxy-6-methyl-9-(4- (1-(methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1263

9-(4-(2-aminoethyl)-3- chlorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1264

9-(4-(2-aminoethyl)-3- chlorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1265

(R)-8-methoxy-6-methyl-9-(4- (1-(methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1266

9-(4-(2-aminopropyl)phenyl)-6- ethyl-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1267

(R)-9-(4-(1-aminoethyl)phenyl)- 6-butyl-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1268

9-(4-(2-aminoethyl)-3- chlorophenyl)-6-chloro-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1269

9-(4-(2-aminopropyl)phenyl)-6- ethyl-8-methoxythieno[2,3-c] quinolin-4(5H)-one 1270

2-(4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)-2-(oxetan-3-yl) acetonitrile 1271

9-(4-(1-amino-2-methylpropan- 2-yl)-3-fluorophenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1272

(R)-6-ethyl-8-hydroxy-9-(4-(1- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1273

9-(4-(1-aminopropan-2-yl)-3- fluorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1274

9-(4-(1-amino-3-methylbutan-2- yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1275

9-(4-(1-aminopropan-2-yl)-3- chlorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1276

9-(4-(1-aminopropan-2-yl)-3- chlorophenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one 1277

9-(4-(1-aminobutan-2-yl)phenyl)- 8-methoxy-6-methylthieno[2, 3-c]quinolin-4(5H)-one 1278

9-(4-(1-amino-2-methylpropan- 2-yl)-3-fluorophenyl)-8- hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1279

9-(4-(1-aminopropan-2-yl)-3- chlorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1280

9-(4-(1-aminopropan-2-yl)-3- chlorophenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1281

9-(4-(2-amino-2-methylpropyl) phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one 1282

9-(4-(2-amino-2-methylpropyl) phenyl)-8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1283

9-(4-(1-amino-3-methylbutan- 2-yl)-3-fluorophenyl)-8-methoxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1284

8-methoxy-6-methyl-9-(4-(3- methyl-1-(methylamino)butan-2- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1285

8-hydroxy-6-methyl-9-(4-(3- methyl-1-(methylamino)butan-2- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1286

9-(3-fluoro-4-(1-(methylamino) propan-2-yl)phenyl)-8-methoxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1287

9-(4-(1-amino-2-methylpropan- 2-yl)-3-fluorophenyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1288

9-(4-(1-amino-3-methylbutan- 2-yl)-3-fluorophenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1289

9-(4-(2-amino-2-methylpropyl) phenyl)-6-bromo-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1290

9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-8-hydroxy-6-methyl thieno[2,3-c]quinolin- 4(5H)-one 1291

9-(4-(1-aminobutan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1292

9-(4-(2-amino-2-methylpropyl) phenyl)-6-bromo-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1293

9-(3-fluoro-4-(1-(methylamino) propan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1294

9-(3-fluoro-4-(3-methyl-1- (methylamino)butan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1295

9-(4-(1-(dimethylamino)-3- methylbutan-2-yl)phenyl)-8- methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1296

9-(4-(1-(dimethylamino)-3- methylbutan-2-yl)-3-fluorophenyl)- 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1297

9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-8-methoxy-6-methyl thieno[2,3-c]quinolin- 4(5H)-one 1298

(R)-8-methoxy-6-methyl-9-(4- (1-(methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1299

9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one 1300

9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1301

8-methoxy-6-methyl-9-(4- (piperidin-3-yl)phenyl)thieno[2,3-c] quinolin-4(5H)-one 1302

8-hydroxy-6-methyl-9-(4- (piperidin-3-yl)phenyl)thieno[2,3- c]quinolin-4(5H)-one 1303

(S)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1304

(S)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1305

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1306

(R)-8-hydroxy-6-methyl-9-(4- (1-(methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1307

(R)-8-hydroxy-6-methyl-9-(4- (1-(methylamino)propan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1308

8-methoxy-3-methyl-3H-pyrrolo [2,3-c]quinolin-4(5H)-one 1309

9-(4-(1-aminobutan-2-yl)phenyl)- 8-hydroxythieno[2,3-c] quinolin-4(5H)-one 1310

(S)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1311

(R)-9-(4-(1-(dimethylamino) propan-2-yl)-3-fluorophenyl)- 8-hydroxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1312

9-(4-(1-aminobutan-2-yl)phenyl)- 6-chloro-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1313

8-hydroxy-3-methyl-3H-pyrrolo [2,3-c]quinolin-4(5H)-one 1314

9-amino-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1315

(R)-9-(3-fluoro-4-(1-(methylamino) propan-2-yl)phenyl)-8- hydroxy-6-methylthieno[2, 3-c]quinolin-4(5H)-one 1316

(R)-9-(3-fluoro-4-(1-(methylamino) propan-2-yl)phenyl)-8- methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1317

(R)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1318

(R)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1319

(R)-9-(4-(1-aminopropan-2-yl)- 3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1320

9-((4-(2-aminoethyl)phenyl) amino)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1321

9-(4-(1-(aminomethyl)cyclobutyl) phenyl)-6-chloro-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1322

(R)-1-(4-(1-aminopropan-2-yl) phenyl)-8-methoxy-3-methyl- 3H-pyrrolo[2,3-c]quinolin-4(5H)- one 1323

8-hydroxy-3-(hydroxymethyl)- 3H-pyrrolo[2,3-c]quinolin- 4(5H)-one 1324

(R)-9-(4-(1-(dimethylamino) propan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1325

9-((4-(aminomethyl)phenyl) amino)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1326

9-((4-(aminomethyl)phenyl) amino)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1327

9-((4-(1-aminopropan-2-yl) phenyl)amino)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1328

9-((4-(1-aminopropan-2-yl) phenyl)amino)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1329

9-(4-(2-aminopropan-2-yl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1330

9-(4-(2-aminopropan-2-yl)phenyl)- 8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1331

9-(4-(3-(aminomethyl)pentan- 3-yl)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1332

9-(4-((R)-1-aminopropan-2-yl) phenyl)-8-hydroxy-2-(1- hydroxyethyl)thieno[2,3-c] quinolin-4(5H)-one 1333

9-(4-((R)-1-aminopropan-2-yl) phenyl)-2-(1-hydroxyethyl)-8- methoxythieno[2,3-c]quinolin- 4(5H)-one 1334

3-(4-((8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)amino)phenyl) propanenitrile 1335

9-((3-(2-aminoethyl)phenyl) amino)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1336

9-((4-(2-aminoethyl)phenyl) amino)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1337

9-(4-(2-(ethylamino)propyl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1338

9-(4-(3-(aminomethyl)pentan- 3-yl)phenyl)-8-methoxythieno[2, 3-c]quinolin-4(5H)-one 1339

9-(4-(3-(aminomethyl)pentan-3- yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1340

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-2,6- dimethylthieno[2,3-c]quinolin- 4(5H)-one 1341

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-8-methoxy-2,6- dimethylthieno[2,3-c]quinolin- 4(5H)-one 1342

9-(4-((R)-1-aminopropan-2-yl) phenyl)-2-(1-hydroxyethyl)-8- methoxy-6-methylthieno[2,3-c] quinolin-4(5H)-one 1343

2-((4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)amino) acetonitrile 1344

(R)-9-(4-(1-aminobutan-2-yl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1345

9-(3-chloro-4-(2-(ethylamino) ethyl)phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1346

9-(4-(3-((dimethylamino)methyl) pentan-3-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c] quinolin-4(5H)-one 1347

(R)-6-chloro-9-(4-(1- (dimethylamino)propan-2- yl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1348

9-(4-(2-(ethylamino)ethyl)phenyl)- 8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1349

9-(4-(2-(ethylamino)ethyl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1350

9-(4-(2-(ethyl(methyl)amino) propyl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1351

2-(hydroxy(piperidin-4-yl) methyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1352

(R)-9-(4-(1-aminobutan-2-yl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1353

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-2-chloro-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1354

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-2-chloro-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1355

8-methoxy-6-methyl-9-(4-(2- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1356

9-(4-(2-(ethyl(methyl)amino) ethyl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1357

9-(4-(3-(aminomethyl)pentan- 3-yl)phenyl)-6-chloro-8- methoxythieno[2,3-c] quinolin-4(5H)-one 1358

9-(4-(3-((dimethylamino)methyl) pentan-3-yl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1359

9-(6-(dimethylamino)pyridin- 3-yl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1360

(R)-9-(4-(1-(dimethylamino) butan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1361

(R)-8-methoxy-6-methyl-9-(4- (1-(methylamino)butan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1362

9-(4-(3-((diethylamino)methyl) pentan-3-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1363

9-(3-chloro-4-(2-(ethylamino) ethyl)phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1364

8-hydroxy-6-methyl-9-(4-(2- (methylamino)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1365

(R)-9-(4-(1-(dimethylamino) butan-2-yl)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1366

(R)-9-(4-(1-(ethyl(methyl) amino)butan-2-yl)phenyl)-8- methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1367

(R)-9-(4-(1-(diethylamino) butan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c] quinolin-4(5H)-one 1368

(R)-9-(4-(1-(ethyl(methyl) amino)butan-2-yl)phenyl)-8- hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1369

2-((4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)(methyl) amino)acetonitrile 1370

2-((4-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)(methyl) amino)acetonitrile 1371

9-(3-chloro-4-(2-(ethyl(methyl) amino)ethyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one 1372

9-(4-(1-((dimethylamino)methyl) cyclobutyl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1373

(R)-9-(4-(1-aminopropyl) phenyl)-6-bromo-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1374

9-(6-(2-aminoethoxy)pyridin-3- yl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1375

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-2-fluoro-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1376

9-(6-(2-aminoethoxy)pyridin-3- yl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1377

9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1378

9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1379

(R)-9-(4-(1-(ethyl(methyl) amino)propan-2-yl)phenyl)-8- hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1380

(R)-8-hydroxy-6-methyl-9-(4- (1-(methylamino)butan-2-yl) phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1381

9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1382

(R)-1-(4-(1-aminopropan-2-yl) phenyl)-8-hydroxy-3-methyl- 3H-pyrrolo[2,3-c]quinolin-4(5H)-one 1383

(R)-9-(4-(1-aminopropan-2-yl) phenyl)-2-fluoro-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1384

9-(6-((2-aminoethyl)amino) pyridin-3-yl)-8-hydroxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1385

9-(6-((2-aminoethyl)amino) pyridin-3-yl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1386

(S)-6-chloro-9-(4-(1-(ethyl (methyl)amino)propan-2-yl) phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1387

(S)-9-(4-(1-(dimethylamino) propan-2-yl)-3-fluorophenyl)- 8-methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1388

(R)-9-(4-(1-(diethylamino) propan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one 1389

9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-8-hydroxythieno[2, 3-c]quinolin-4(5H)-one 1390

9-(4-(1-amino-2,2,2-trifluoroethyl) phenyl)-6-bromo-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1391

9-(4-(1-(aminomethyl)cyclopropyl) phenyl)-6-bromo-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1392

(4-(8-hydroxy-6-methyl-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl) methanesulfonamide 1393

8-methoxy-6-methyl-9-(4-(2- (methylsulfinyl)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1394

8-hydroxy-6-methyl-9-(4- ((methylsulfonyl)methyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1395

(4-(8-methoxy-6-methyl-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl) methanesulfonamide 1396

9-(4-((2-aminoethyl)(methyl) amino)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1397

(R)-N-(2-(2-fluoro-4-(8-hydroxy- 6-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) phenyl)propyl)methanesulfonamide 1398

(R)-N-(2-(2-fluoro-4-(8-methoxy- 6-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl) phenyl)propyl)methanesulfonamide 1399

(S)-9-(4-(1-(dimethylamino)propan- 2-yl)-3-fluorophenyl)-8- hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one 1400

9-(4-((2-aminoethyl)(methyl) amino)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1401

9-(4-(1-(aminomethyl)cyclopropyl) phenyl)-6-bromo-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1402

2-(6-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)pyridin-3-yl) acetonitrile 1403

8-hydroxy-6-methyl-9-(4-(2- (methylsulfinyl)ethyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1404

8-methoxy-6-methyl-9-(4- ((methylsulfonyl)methyl)phenyl) thieno[2,3-c]quinolin-4(5H)-one 1405

5-(8-methoxy-6-methyl-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)nicotinamide 1406

2-(5-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl)propanenitrile 1407

2-(4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propanamide 1408

9-(6-(1-aminopropan-2-yl) pyridin-3-yl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1409

2-(5-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)pyridin-2-yl)-2- methylpropanenitrile 1410

2-hydroxy-2-(4-(8-hydroxy-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propane- 1-sulfonamide 1411

N-(tert-butyl)-2-hydroxy-2-(4- (8-methoxy-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl) propane-1-sulfonamide 1412

2-(4-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propanamide 1413

2-(4-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)propane-1-sulfonamide 1414

9-(4-(2-amino-1-fluoroethyl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1415

9-(6-(1-aminopropan-2-yl) pyridin-3-yl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1416

2-(5-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)pyridin-2-yl)-2- methylpropanenitrile 1417

2-(5-(8-hydroxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl)-2- methylpropanenitrile 1418

2-(5-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl)-2- methylpropanenitrile 1419

2-(4-(8-hydroxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propane- 1-sulfonamide 1420

9-(4-(2-amino-1-hydroxyethyl) phenyl)-8-methoxy-6-methylthieno [2,3-c]quinolin-4(5H)-one 1421

9-(6-(1-amino-2-methylpropan- 2-yl)pyridin-3-yl)-8-hydroxythieno [2,3-c]quinolin-4(5H)-one 1422

N-cyclopropyl-1-(4-(8-methoxy- 6-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl) methanesulfonamide 1423

2-(5-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl)propanenitrile 1424

(R)-N-(2-(4-(8-methoxy-6- methyl-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl) propyl)methanesulfonamide 1425

N-ethyl-1-(4-(8-methoxy-6- methyl-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl) methanesulfonamide 1426

9-(6-(1-aminopropan-2-yl) pyridin-3-yl)-8-methoxythieno [2,3-c]quinolin-4(5H)-one 1427

N-cyclopropyl-1-(4-(8-hydroxy- 6-methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl) methanesulfonamide 1428

1-(5-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) pyridin-2-yl) cyclopropanecarbonitrile 1429

N-ethyl-1-(4-(8-hydroxy-6-methyl- 4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl) methanesulfonamide 1430

1-(4-(8-methoxy-6-methyl-4- oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl) ethanesulfonamide 1431

1-(4-(8-methoxy-4-oxo-4,5- dihydrothieno[2,3-c]quinolin-9-yl) phenyl)ethanesulfonamide 1432

(R)-N-(2-(4-(8-methoxy-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl) methanesulfonamide 1433

(R)-N-(2-(4-(8-hydroxy-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl)- N-methylmethanesulfonamide 1434

(R)-N-(2-(4-(8-hydroxy-6- methyl-4-oxo-4,5-dihydrothieno [2,3-c]quinolin-9-yl)phenyl)propyl) methanesulfonamide 1435

(R)-N-(2-(4-(8-hydroxy-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl) methanesulfonamide 1436

(R)-N-(2-(4-(8-methoxy-4-oxo- 4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl)- N-methylmethanesulfonamide 1437

(R)-N-(2-(4-(8-hydroxy-6-methyl- 4-oxo-4,5-dihydrothieno[2,3-c] quinolin-9-yl)phenyl)propyl)- N-methylmethanesulfonamide 1438

(R)-N-(2-(4-(8-methoxy-6- methyl-4-oxo-4,5-dihydrothieno[2, 3-c]quinolin-9-yl)phenyl)propyl)- N-methylmethanesulfonamide

The compound of formula (I) of the present invention may be in the form of a pharmaceutically acceptable salt derived from an inorganic or organic acid. Representative examples of the pharmaceutically acceptable salt derived from an inorganic or organic acid include salts obtained by adding to the compound of formula (I) an inorganic acid including, but not limited to hydrochloric acid, hydrobromic acid, phosphoric acid or sulfonic acid, or organic carboxylic acids such as acetic acid, trifluoroacetic acid, citric acid, formic acid, maleic acid, oxalic acid, succinic acid, benzoic acid, tartaric acid, fumaric acid, mandelic acid, ascorbic acid or malic acid, methanesulfonic acid, or para toluenesulfonic acid, which do not limit its scope. Such acids may be prepared by the conventional processes, and other acids, which themselves are not pharmaceutically acceptable, including oxalic acid may be employed in the preparation of the salts.

Alternatively, the compound of formula (I) of the present invention may also be in the form of a pharmaceutically acceptable salt derived from an inorganic or organic base include salts obtained by adding an inorganic or organic base. For example, alkalis including sodium hydroxide or potassium hydroxide, or alkaline earth metal hydroxides including calcium hydroxide, magnesium hydroxide, aluminum hydroxide or ammonium hydroxide may be used for the preparation of inorganic salt of the compound. Further, organic bases including triethylamine or diisopropylethylamine may also be used for the preparation of organic salt of the compound.

The compounds of formula (I) may be prepared as in Scheme (I) and (II).

A variety of acids A whose structure is defined by the cycles (Cy₁₋₃) shown in Scheme I, were converted to the corresponding acid chloride and then coupled with the requisite aniline to afford coupled products B. In the case where R₅=H, the amide was protected to obtain intermediates C which subsequently underwent the key intramolecular Heck cyclization using bis-tri-t-butyl phosphine as the catalyst of choice. This provided tricycles D which included some compounds of Formula I, II and III. In some instances tricycles D were brominated using NBS or nitrated using potassium nitrate and trifluoroacetic anhydride to provide products E (Scheme I).

The aryl bromides F were either purchased or prepared and then converted to the corresponding boronic acids or boronate esters G via standard conditions. Bromides E underwent Suzuki or Buchwald type cross-coupling reactions with the requisite boronate esters or boronic acids G to afford compounds H some of which are compounds of Formula I, II and III. In cases where R₃=OCH₃, treatment of compounds H (via path i) with boron tribromide or aluminum chloride provided the de-methylated compounds I which includes compounds of Formula I, II and III (Scheme II). Additionally, treatment of compounds H (via path ii) with NCS or NBS afforded compounds I containing a halogen at R₁. These halogenated compounds were treated with boron tribromide or aluminum chloride to provide the de-methylated compounds I. Finally, compounds with R₁=Br were reacted with trimethylboroxine and palladium catalyst to afford compounds J of formula I, II and III where R₁=CH₃. Treatment of these compounds with boron tribromide afforded compounds of formula I, II and III.

A salt, hydrate, solvate and isomer of the inventive compound of formula (I) or (II) may be prepared by employing any of the known methods. The inventive compound of formula (I) or (II), or a salt, hydrate, solvate or isomer thereof, may be used for the treatment of PBK-dependent diseases such as cancer. The treatment of PBK-dependent diseases can be accomplished by way of inhibiting PBK activity. The inventive compound typically have an IC₅₀ value (micro M) in the range of 0.0001 to 100, for example 0.001 to 50, preferably 0.001 to 10, more preferably 0.001 to 5.

Accordingly, the present invention includes a pharmaceutical composition that includes a therapeutically effective amount of the compound of formula (I) or (II), a salt, hydrate, solvate or isomer thereof as an active ingredient and a pharmaceutically acceptable carrier. The pharmaceutical composition of the present invention can be used to treat or prevent PBK-dependent diseases.

A pharmaceutical formulation may be prepared in accordance with any of the conventional procedures. In preparing the formulation, the active ingredient is preferably admixed or diluted with a carrier, or enclosed within a carrier, sachet or other container. The carrier may be a solid, semi-solid or liquid material acting as a vehicle, excipient or medium for the active ingredient. The formulations may be in the form of a tablet, pill, powder, sachet, elixir, suspension, emulsion, solution, syrup, aerosol, soft and hard gelatin capsule, sterile injectable solution, sterile packaged powder and the like.

Examples of suitable carriers, excipients, and diluents are lactose, dextrose, sucrose, sorbitol, mannitol, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, and mineral oil. The formulations may additionally include fillers, antiemulsifiers, preservatives and the like. The compositions of the invention may be formulated to provide immediate, sustained or delayed release of the active ingredient after their administration to a mammal by employing any of the procedures well known in the art.

The pharmaceutical composition of the present invention can be administered via various routes including oral, transdermal, subcutaneous, intravenous and intramuscular administration.

In addition to the above, the present composition may contain other pharmaceutical active ingredients so long as they do not inhibit the in vivo function of the compound of the present invention. The compounds as disclosed herein can be co-administered with a second therapeutic agent, such as a chemotherapeutic agent. The term “co-administer” means to administer more than one active agent, such that the duration of physiological effect of one active agent overlaps with the physiological effect of a second active agent. For systematic agents, the term co-administer means that more than one active agent is present in the bloodstream during at least one time point. Co-administration includes administering two active agents simultaneously, approximately simultaneously, or sequentially in any order. In some embodiments, co-administration can be accomplished by co-formulation, i.e., preparing a single dosage unit including both active agents.

“Treating” the disease includes one or more of: addressing a physiological cause of the disease, addressing a physiological cause of a disease symptom, reducing the severity of the disease, ameliorating a symptom of the disease, and shortening the duration of the disease. “Preventing” the disease includes eliminating or delaying the onset of a disease or its symptoms.

The compounds disclosed herein can be used to treat or prevent PBK-dependent diseases, including cancer. It has been shown that PBK is a target for treating cancers, such as breast cancer (Example 504 of the present specification), bladder cancer (WO2006/085684), and small cell lung cancer (WO2007/013665). Accordingly, cancers to be targeted include, but are not limited to, breast cancer, bladder cancer, and small cell lung cancer. For example, the present invention provides methods for treating or preventing PBK-dependent diseases, including cancer, in a subject by administering to said subject the compounds disclosed herein.

In a preferred embodiment, such compound can be administered to the subject in the form of pharmaceutical composition including the compound of the present invention and pharmaceutically or physiologically acceptable carrier. The pharmaceutical composition of the present invention can be administered via various routes including oral, transdermal, subcutaneous, intravenous and intramuscular introduction for treating PBK dependent diseases, including cancer, in a subject.

In another embodiment, the present invention also provides the use of the compound of the present invention in manufacturing a pharmaceutical composition for treating a PBK dependent diseases including cancer. For example, the present invention relates to a use of the compound of the present invention for manufacturing a pharmaceutical composition for treating PBK dependent diseases, including cancer. In another embodiment, the compounds of the present invention can be used in treating PBK dependent diseases, including cancer.

In another embodiment, the present invention also provides a method or process for manufacturing a pharmaceutical composition for treating a PBK dependent diseases including cancer, wherein the method or process includes a step for admixing an active ingredient with a pharmaceutically or physiologically acceptable carrier, wherein the active ingredient is the compound of the present invention.

The dosage and method of administration vary according to the body weight, age, and symptoms of the patient; however, one skilled in the art can suitably select them.

For example, the dose is generally about 0.1 mg to about 100 mg per day, preferably about 1.0 mg to about 50 mg per day and more preferably about 1.0 mg to about 20 mg per day, when administered orally to a normal adult human (weight 60 kg).

When administering the compound parenterally, in the form of an injection to a normal adult human (weight 60 kg), although there are some differences according to the patient, target organ, symptoms and method of administration, it is convenient to intravenously inject a dose of about 0.01 mg to about 30 mg per day, preferably about 0.1 to about 20 mg per day and more preferably about 0.1 to about 10 mg per day. In the case of other animals, the appropriate dosage amount may be routinely calculated by converting to 60 kg of body weight.

EXAMPLES

The following examples are intended to further illustrate the present invention without limiting its scope.

General Procedure A (Scheme I):

Step 1: To a suspension of the requisite carboxylic acid A (1 mol) in CH₂Cl₂ (0.1-0.5 M) at room temperature was added (COCl)₂ (2 mol) followed by the addition of catalytic DMF. The reaction mixture was stirred at room temperature for 18 h, concentrated and dried under high vacuum to obtain the intermediate acid chloride. The acid chloride was dissolved in CH₂Cl₂ (0.1-0.3 M) followed by the addition of Et₃N (1.5-2 mol) and the requisite aniline (1.1 mol) and the reaction was stirred at room temperature for 18 h. The reaction mixture was concentrated, triturated with an appropriate solvent or purified by flash chromatography to obtain amide B as a solid. Step 2: To a solution of amide B (1 mol) in THF (0.1-0.3 M) at 0° C. was added NaH (1.2 mol) and the reaction was warmed up to 45° C. for 15 min and cooled to 0° C. followed by the addition of (Boc)₂O (2 mol). The reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was quenched by slowly pouring it into a stirred solution of water and satd aq NaHCO₃ at 0° C. The mixture was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over Na₂SO₄ and concentrated. The residue was triturated with an appropriate solvent or purified by flash chromatography to obtain C as a solid. Step 3: Intermediate C (1 mol), bis(tri-tert-butylphosphine)palladium (5 mol %) and potassium acetate (4 mol) were added to a Parr pressure reactor followed by the addition of dimethyl acetamide (0.3 M). The reaction mixture was sparged with nitrogen for 30 min followed by heating at 140-150° C. for 4 h. The reaction mixture was cooled and quenched by pouring into brine at 0° C. The resulting precipitate was filtered and the filter cake was washed with water and ether to obtain crude D as a solid. Step 4: To a solution of crude D (1 mol) in CH₂Cl₂:AcOH (1:1) was added NBS (1 mol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was quenched by pouring slowly into a stirred solution of ice and satd aq Na₂CO₃. Once the aqueous layer was at pH 8 the layers were separated and the CH₂Cl₂ layer was concentrated, triturated with acetonitrile and filtered to obtain E as solid.

Example 392 4-(tert-Butyldimethylsilyloxy)aniline

To a solution of 4-aminophenol (11 g, 100 mmol) and imidazole (10 g, 150 mmol) in THF (250 mL) was added tert-butyldimethylsilyl chloride (18 g, 120 mmol) and the reaction was stirred at room temperature for 18 h. The reaction mixture was poured into water and extracted with diethyl ether. The combined organic layers were dried over Na₂SO₄, filtered, concentrated and the residue was purified by column chromatography to afford the desired product (15 g, 67%): ESI MS m/z 224 [C₁₂H₂₁NOSi+H]⁺.

Example 393 3-Bromo-N-[4-(tert-butyldimethylsilyloxy)phenyl]thiophene-2-carboxamide

Following Step 1 from General Procedure A, 5-bromothiophene-2-carboxylic acid (3.0 g, 14 mmol) was reacted with 4-(tert-butyldimethylsilyloxy)aniline (4.2 g, 19 mmol) to afford the desired product (4.4 g, 73%) as a solid: ESI MS m/z 413 [C₁₇H₂₂BrNO₂SSi+H]⁺.

Example 394 tert-Butyl 3-Bromothiophene-2-carbonyl[4-(tert-butyldimethylsilyloxy)phenyl]carbamate

Following Step 2 from General Procedure A, 3-bromo-N-[4-(tert-butyldimethylsilyloxy)phenyl]thiophene-2-carboxamide (4.4 g, 11 mmol) was reacted with di-tert-butyl dicarbonate (4.6 g, 21 mmol) to afford the desired product (1.5 g, 28%) as a solid: ESI MS m/z 513 [C₂₂H₃₀BrNO₄SSi+H]⁺.

Example 395 8-(tert-Butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one

Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl[4-(tert-butyldimethylsilyloxy)phenyl]carbamate (1.0 g, 2.0 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (50 mg, 0.098 mmol) to afford the desired product (740 mg, quant.) as a solid: ESI MS m/z 332 [C₁₇H₂₁NO₂SSi+H]⁺.

Example 396 9-Bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one

Following Step 4 from General Procedure A, 8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one (740 mg, 2.2 mmol) was reacted with N-bromosuccinimide (480 mg, 2.7 mmol) to afford the desired product (340 mg, 37%) as a brown solid: ESI MS m/z 411 [C₁₇H₂₀BrNO₂SSi+H]⁺.

Example 397 N-(2-Bromo-4-methoxyphenyl)-5-methyl-N-(5-methylthiophene-2-carbonyl)thiophene-2-carboxamide

Following Step 1 from General Procedure A, 5-methylthiophene-2-carboxylic acid (8.5 g, 60 mmol) was reacted with 2-bromo-4-methoxyaniline (6.7 g, 30 mmol) to afford the desired product (5.0 g, 57%) as a solid: ESI MS m/z 327 [C₁₃H₁₂BrNO₂S+H]⁺.

Example 398 8-Methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one

Following Step 3 from General Procedure A, N-(2-bromo-4-methoxyphenyl)-5-methyl-N-(5-methylthiophene-2-carbonyl)thiophene-2-carboxamide (500 mg, 1.1 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (45 mg, 0.089 mmol) to afford the desired product (1.3 g, 48%) as a green solid: ESI MS m/z 246 [C₁₃H₁₁NO₂S+H]⁺.

Example 399 9-Bromo-8-methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one

Following Step 4 from General Procedure A, 8-methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one (1.4 g, 5.7 mmol) was reacted with N-bromosuccinimide (1.2 g, 6.9 mmol) to afford the desired product (740 mg, 40%) as a brown solid: ESI MS m/z 325 [C₁₃H₁₀BrNO₂S+H]⁺.

Example 400 3-bromo-N-(2-fluoro-4-methoxyphenyl)thiophene-2-carboxamide

Following Step 1 from General Procedure A, 3-bromothiophene-2-carboxylic acid (7.3 g, 35 mmol) was reacted with 2-fluoro-4-methoxyaniline (5.0 g, 35 mmol) to afford the desired product (10 g, 90%) as an orange solid: ESI MS m/z 331 [C₁₂H₁FNO₂S+H]⁺.

Example 401 tert-butyl 3-bromothiophene-2-carbonyl(2-fluoro-4-methoxyphenyl)carbamate

Following Step 2 from General Procedure A, 3-bromo-N-(2-fluoro-4-methoxyphenyl)thiophene-2-carboxamide (12 g, 35 mmol) was reacted with di-tert-butyl dicarbonate (12 g, 53 mmol) to afford the desired product (14 g, >99%) as an orange solid: ESI MS m/z 331 [C₁₂H₁₀FNO₂S+H]⁺.

Example 402 6-Fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl(2-fluoro-4-methoxyphenyl)carbamate (2.0 g, 4.6 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (100 mg, 0.20 mmol) to afford the desired product (950 mg, 80%) as a dark brown solid: ESI MS m/z 250 [C₁₂H₈FNO₂S+H]⁺.

Example 403 9-Bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following Step 4 from General Procedure A, 6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.0 g, 4.0 mmol) was reacted with N-bromosuccinimide (570 mg, 4.8 mmol) to afford the desired product (800 mg, 61%) as a brown solid: ESI MS m/z 329 [C₁₂H₇BrFNO₂S+H]⁺.

Example 404 3-Bromo-N-(2,3-difluoro-4-methoxyphenyl)thiophene-2-carboxamide

Following Step 1 from General Procedure A, 3-bromothiophene-2-carboxylic acid (1.3 g, 6.3 mmol) was reacted with 2,3-difluoro-4-methoxyaniline (960 mg, 7.5 mmol) to afford the desired product (2.2 g, >99%): ESI MS m/z 349 [C₁₂H₈BrF₂NO₂S+H]⁺.

Example 405 tert-Butyl 3-Bromothiophene-2-carbonyl(2,3-difluoro-4-methoxyphenyl)carbamate

Following Step 2 from General Procedure A, 3-bromo-N-(2,3-difluoro-4-methoxyphenyl)thiophene-2-carboxamide (2.4 g, 7.00 mmol) was reacted with di-tert-butyl dicarbonate (330 mg, 14 mmol) to afford the desired product (2.1 g, 67%) as a white solid: ESI MS m/z 448 [C₁₇H₁₆BrF₂NO₄S+H]⁺.

Example 406 6,7-Difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl(2,3-difluoro-4-methoxyphenyl)carbamate (1.4 g, 3.1 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (80 mg, 0.15 mmol) to afford the desired product (58 mg, 65%) as a brown solid: ESI MS m/z 268 [C₁₂H₇F₂NO₂S+H]⁺.

Example 407 9-Bromo-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following Step 4 from General Procedure A, 6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (300 mg, 1.1 mmol) was reacted with N-bromosuccinimide (400 mg, 2.2 mmol) to afford the desired product (200 mg, 57%) as a yellow solid: ESI MS m/z 347 [C₁₂H₆BrF₂NO₂S+H]⁺.

Example 510 3-bromo-N-(4-methoxy-2-methylphenyl)thiophene-2-carboxamide

Following Step 1 from General Procedure A, 3-bromothiophene-2-carboxylic acid (6.7 g, 49 mol) was reacted with 2-methyl-4-methoxyaniline (12 g, 53 mmol) to afford the desired product (13 g, 80%) as an orange solid: ESI MS m/z 331 [C₁₂H₁₀FNO₂S+H]⁺.

Example 511 tert-butyl 3-bromothiophene-2-carbonyl(4-methoxy-2-methylphenyl)carbamate

Following Step 2 from General Procedure A, 3-bromo-N-(4-methoxy-2-methylphenyl)thiophene-2-carboxamide (12 g, 37 mmol) was reacted with di-tert-butyl dicarbonate (9.6 g, 44 mmol) to afford the desired product (15 g, 96%) as an orange solid: ESI MS m/z 331 [C₁₂H₁₀FNO₂S+H]⁺.

Example 512 8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl(4-methoxy-2-methylphenyl)carbamate (14 g, 33 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (750 mg, 1.5 mmol) to afford the desired product (7.0 g, 85%) as a dark brown solid: ESI MS m/z 250 [C₁₂H₈FNO₂S+H]⁺.

Example 513 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

Following Step 4 from General Procedure A, 8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (6.4 g, 26 mmol) was reacted with N-bromosuccinimide (5.0 g, 26 mmol) to afford the desired product (7.0 g, 82%) as a brown solid: ESI MS m/z 329 [C₁₂H₇BrFNO₂S+H]⁺.

Example 514 3-Bromo-N-(4-methoxyphenyl)thiophene-2-carboxamide

Following Step 1 from General Procedure A, 5-bromothiophene-2-carboxylic acid (75 g, 360 mmol) was reacted with 4-methoxyaniline (54 g, 430 mmol) to afford the desired product (110 g, 93%) as a solid: ESI MS m/z 313 [C₁₂H₁₀BrNO₂S+H]⁺.

Example 515 tert-Butyl 3-bromothiophene-2-carbonyl(4-methoxyphenyl)carbamate

Following Step 2 from General Procedure A, 3-Bromo-N-(4-methoxyphenyl)thiophene-2-carboxamide (60 g, 190 mmol) was reacted with di-tert-butyl dicarbonate (83 g, 380 mmol) to afford the desired product (65 g, 82%) as a solid: ESI MS m/z 413 [C₁₇H₁₈BrNO₄S+H]⁺.

Example 516 8-Methoxythieno[2,3-c]quinolin-4(5H)-one

Following Step 3 from General Procedure A, tert-butyl 3-bromothiophene-2-carbonyl (4-methoxyphenyl)carbamate (62 g, 150 mmol) was reacted with bis(tri-tert-butylphosphine) palladium (3.7 g, 5 mol %) to afford the crude desired product (26 g) as a grey-brown solid: ESI MS m/z 232 [C₂H₉NO₂S+H]⁺.

Example 517 9-Bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

General Procedure B (Scheme II):

To a solution of bromides E (1 mmol) in DMF was added Cs₂CO₃ (3 mmol), Pd(dppf)Cl₂ (0.1 mmol) and boronate esters or acids G (1-2 mmol) and the reaction was heated at 80° C. for 18 h. The reaction mixture was cooled, concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) or preparatory HPLC (C18 silica, acetonitrile/water with 0.05% TFA gradient) to obtain the desired products H. In some instances the desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.

General Procedure C (Scheme II):

The compound from General Procedure B (1 mmol) was dissolved in TFA (10 mmol) and stirred at room temperature for 2 h and concentrated. The residue was eluted through an ion-exchange column (using methanol and 7 N methanol in ammonia) to obtain the desired product as the free base. In some instances the desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.

General Procedure D-1 (Scheme II):

The requisite compound (1 mmol) was dissolved in methanol followed by the addition of 2 N HCl in diethylether (100 mmol). The reaction mixture was stirred at room temperature for 2 h and filtered or concentrated to obtain the desired product as the hydrochloride salt.

General Procedure D-2 (Scheme II):

The requisite compound was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.

General Procedure D-3 (Scheme II):

The requisite compound (1 mmol) was dissolved in aqueous HCl (100 mmol) and stirred concentrated at room temperature for 2 h, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.

General Procedure E—One Pot (Scheme II):

To a solution of aryl bromides F (1 mmol) in dioxane was added KOAc (2 mmol), Pd(dppf)Cl₂ (0.1 mmol) and bis(pinacolato)diboron (1.5 mmol) and the reaction was heated at 90° C. until the aryl bromide was consumed. To the reaction mixture was added Cs₂CO₃ (2 mmol) and bromides E (0.5 mmol) and heating was continued for 18 h. The reaction mixture was cooled, concentrated and purified by chromatography (silica, ethyl acetate/hexanes gradient) or preparatory HPLC (C18 silica, acetonitrile/water with 0.05% TFA gradient) to obtain the desired products I. In some instances the desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.

General Procedure F (Scheme II):

To a solution or suspension of compounds H, I, or J (R₃═OCH₃) (1 mmol) in CH₂Cl₂ at 0° C. was added BBr₃ (6-10 mmol) and the reaction was warmed to room temperature for 18 h or until the starting material disappeared by LCMS analysis. The reaction was quenched by pouring onto ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and eluted through an ion-exchange column (using methanol and 7 N methanol in ammonia) to obtain the desired product. In some instances the desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt.

General Procedure G (Scheme II):

To a solution of aryl bromides F (1 mmol) in dioxane was added KOAc (2 mmol), Pd(dppf)Cl₂ (0.1 mmol) and bis(pinacolato)diboron (1.5 mmol) and the reaction was heated at 90° C. for 18 h. The reaction mixture was cooled, concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product.

General Procedure H (Scheme II):

To a solution requisite compound H (1.0 mmol) in DMF was added N-chlorosuccinimide (1.2 mmol) and the reaction was stirred at room temperature for 30 min and heated at 60° C. for 2 h. The reaction mixture was concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product I.

General Procedure I (Scheme II):

To a solution requisite compound H (1.0 mmol) in DMF was added N-bromosuccinimide (1.2 mmol) and the reaction was stirred at room temperature for 30 min and heated at 50° C. for 2 h. The reaction mixture was concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product I.

General Procedure J (Scheme II):

To a solution requisite compound I (1.0 mmol) in toluene, was added tripotassium phosphate (4.0 mmol), trimethylboroxine (3.0 mmol), water (0.60 M) and Pd(PPh₃)₄ (0.10 mmol) the reaction mixture degassed and heated at 120° C. for 2 hr. The reaction mixture was cooled, concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product J.

Example 518 (S)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-1)-one (670 mg, 2.2 mmol) was reacted with (S)-tert-butyl methyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate (1.3 g, 3.4 mmol) to afford the desired product (700 mg, 48%) as a light brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 519 (S)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (240 mg, 0.32 mmol) was reacted with (S)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (3.5 g, 9.7 mmol) to afford the desired product (1.4 g, 32%) as a light brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 520 tert-Butyl(1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (830 mg, 2.7 mmol) was reacted with tert-butyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methylcarbamate (1.5 g, 4.0 mmol) to afford the desired product (670 mg, 52%) as a light brown solid: ESI MS m/z 477 [C₂₇H₂₈N₂O₄S+H]⁺.

Example 521 tert-Butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate

Following General Procedure B, 9-bromo-8-met oxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with tert-butyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methylcarbamate (260 mg, 0.69 mmol) to afford the desired product (150 mg, 68%) as a light brown solid: ESI MS m/z 491 [C₂₈H₃₀N₂O₄S+H]⁺.

Example 522 (S)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.5 g, 8.1 mmol) was reacted with (S)-tert-butylmethyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate (4.6 g, 12 mmol) to afford the desired product (1.9 g, 50%) as a light brown solid: ESI MS m/z 47 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 523 (S)-tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with (S)-tert-butyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (251 mg, 0.69 mmol) to afford the desired product (140 mg, 62%) as a light brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 524 (S)-tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with (S)-tert-butyl2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (251 mg, 0.69 mmol) to afford the desired product (135 mg, 62%) as a light brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 525 tert-Butyl 2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (3.0 g, 9.7 mmol) was reacted with tert-butyl 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate (5.53 g, 14.5 mmol) to afford the desired product (2.65 g, 57%) as a light brown solid. ESI MS m/z 485 [C₂₅H₂₅ClN₂O₄S+H]⁺.

Example 526 (R)-tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with (R)-tert-butylmethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (250 mg, 0.69 mmol to afford the desired product (145 mg, 66%) as a light brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 527 (R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one 1.4 g, 4.4 mmol) was reacted with (R)-tert-butylmethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (2.4 g, 6.6 mmol) to afford the desired product (1.4 g, 66%) as a light brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 528 tert-Butyl 2-(2-fluoro-4-(8-methoxy-1-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.4 g, 4.3 mmol) was reacted with tert-butyl2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methylpropylcarbamate (2.5 g, 6.4 mmol) to afford the desired product (1.7 g, 79%) as a light brown solid. ESI MS m/z 497 [C₂₇H₂₁FN₂O₄S+H]⁺.

Example 529 tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methylpropylcarbamate (270 mg, 0.64 mmol) to afford the desired product (130 mg, 56%) as a light brown solid: ESI MS m/z 511 [C₂₈H₃₁FN₂O₄S+H]⁺.

Example 530 tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate

Following General Procedure B, 9-brom-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (240 mg, 0.64 mmol) to afford the desired product (75 mg, 33%) as a light brown solid: ESI MS m/z 493 [C₂₈H₁₂N₂O₄S+H]⁺.

Example 531 (S)-tert-Butyl 1-(4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (640 mg, 2.1 mmol) was reacted with (S)-tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (1.13 g, 3.12 mmol) to afford the desired product (680 mg, 71%) as a light brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 532 tert-Butyl(1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.46 mmol) was reacted with tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methylcarbamate (270 mg, 0.70 mmol to afford the desired product (105 mg, 45%) as a light brown solid: ESI MS m/z 505 [C₂₉H₃₂N₂O₄S+H]⁺.

Example 533 tert-Butyl(1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.9 g, 6.0 mmol) was reacted with tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methylcarbamate (3.5 g, 9.0 mmol) to afford the desired product (1.5 g, 33%) as a light brown solid: ESI MS m/z 491 [C₂₈H₃₀N₂O₄S+H]⁺.

Example 534 tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (840 mg, 2.7 mmol) was reacted with tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (1.5 g, 4.0 mmol) to afford the desired product (820 mg, 43%) as a light brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 535 tert-Butyl ethyl(1-((8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)carbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (770 mg, 2.5 mmol) was reacted with tert-butyl ethyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (1.4 g, 3.7 mmol) to afford the desired product (450 mg, 40%) as a light brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 536 tert-Butyl4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.4 g, 7.6 mmol) was reacted with tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)carbamate (4.2 g, 11 mmol) to afford the desired product (2.1 g, 40%) as a light brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 537 (S)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.6 g, 8.2 mmol) was reacted with (S)-tert-butyl methyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate (4.6 g, 12 mmol) to afford the desired product (1.9 g, 50%) as a light brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 538 (S)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (380 mg, 1.2 mmol) was reacted with (S)-tert-butyl2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (400 mg, 1.1 mmol) to afford the desired product (190 mg, 36%) as a yellow solid: ESI MS m/z 497 [C₂₇H₂₉FN₂O₄S+H]⁺.

Example 539 tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (800 mg, 2.58 mmol) was reacted with tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (1.2 g, 3.09 mmol) to afford the desired product (250 mg, 20%) as a yellow solid: ESI MS m % z 493 [C₂₈H₃₂N₂O₄S+H]⁺.

Example 540 tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (500 mg, 1.54 mmol) was reacted with tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (590 mg, 1.9 mmol) to afford the desired product (120 mg, 15%) as a yellow solid: ESI MS m/z 507 [C₂₉H₃₄N₂O₄S+H]⁺.

Example 541 (R)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (770 mg, 2.4 mmol) was reacted with (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (770 mg, 2.0 mmol) to afford the desired product (500 mg, 49%) as a yellow solid: ESI MS m/z 497 [C₂₇H₂₉FN₂O₄S+H]⁺.

Example 542 (R)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (180 mg, 0.57 mmol) was reacted with (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl(methyl)carbamate (150 mg, 0.38 mmol) to afford the desired product (190 mg, 36%) as a yellow solid: ESI MS m/z 511 [C₂₈H₃₁FN₂O₄S+H]⁺.

Example 543 (R)-tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (900 mg, 2.9 mmol) was reacted with (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (900 mg, 2.7 mmol) to afford the desired product (190 mg, 15%) as a yellow solid: ESI MS m % z 493 [C₂₈H₃₂N₂O₄S+H]⁺.

Example 544 tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (900 mg, 2.8 mmol) was reacted with ter-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (1.3 g, 3.3 mmol) to afford the desired product (200 mg, 27%) as a yellow solid: ESI MS m/z 497 [C₂₇H₂₉FN₂O₄S+H]⁺.

Example 545 tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methyl butylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (170 mg, 0.50 mmol) was reacted with tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutylcarbamate (200 mg, 0.50 mmol) to afford the desired product (65 mg, 25%) as a yellow solid: ESI MS m/z 525 [C₂₉H₃₃FN₂O₄S+H]⁺.

Example 546 tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (380 mg, 1.16 mmol) was reacted with tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl(methyl)carbamate (400 mg, 1.1 mmol) to afford the desired product (190 mg, 36%) as a yellow solid: ESI MS m/z 511 [C₂₈H₃₁FN₂O₄S+H]⁺.

Example 547 tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl-3-methylbutyl(methyl)carbamate

Following General Procedure, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (265 mg, 0.81 mmol) was reacted with tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutyl(methyl)carbamate (300 mg, 0.89 mmol) to afford the desired product (80 mg, 18%) as a yellow solid: ESI MS m/z 539 [C₃₀H₃₅FN₂O₄S+H]⁺.

Example 548 (R)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (1.0 g, 3.3 mmol) was reacted with (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (1.1 g, 3.0 mmol) to afford the desired product (510 mg, 34%) as a yellow solid: ESI MS m/z 497 [C₂₇H₁₉FN₂O₄S+H]⁺.

Example 549 tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (440 mg, 1.4 mmol) was reacted with tert-butyl methyl(3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)carbamate (600 mg, 1.5 mmol) to afford the desired product (100 mg, 14%) as a yellow solid: ESI MS m/z 521 [C₃₀H₃₆N₂O₄S+H]⁺.

Example 550 (S)-tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-methylthieno[2,3-c]quinolin-4(5H)-one) (840 mg, 2.6 mmol) was reacted with (S)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (900 mg, 2.4 mmol) to afford the desired

Example 551 (R)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one (1.2 g, 4.0 mmol) was reacted with (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (2.2 g, 6.1 mmol) to afford the desired product (900 mg, 48%) as a yellow solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 1057 N-(1-Hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (530 mg, 1.8 mmol) was reacted with N-(1-hydroxypropan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (750 mg, 2.02 mmol) to afford the desired product (150 mg, 20%) as a yellow solid: ESI MS m/z 445 [C₂₁H₂₀N₂O₅S₂+H]⁺.

Example 1238 3-(4-(8-Methoxy-6-methyl-4-oxo-4,5-dihydrothieno)[2,3-c]quinolin-9-yl)phenyl)propanenitrile

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (325 mg, 1.0 mmol) was reacted 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (330 mg, 1.3 mmol) to afford the desired product (140 mg, 37%) as a yellow solid: ESI MS m/z 375 [C₂₂H₁₈N₂O₂S+H]⁺.

Example 552 tert-Butyl 2-cyclopentyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (500 mg, 1.6 mmol) was reacted with tert-butyl 2-cyclopentyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate (1.3 g, 3.2 mmol) to afford the desired product (150 mg, 19%) as a yellow solid: ESI MS m/z 519 [C₃₀H₃₄N₂O₄S+H]⁺.

Example 553 tert-Butyl 3-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)piperidine-1-carboxylate

Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (190 mg, 0.58 mmol) was reacted with tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate (180 mg, 0.46 mmol) to afford the desired product (79 mg, 34%) as a yellow solid: ESI MS m % z 505 [C₂₉H₃₂N₂O₄S+H]⁺.

Example 554 tert-Butyl 2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino ethylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (86 mg, 0.26 mmol) was reacted with tert-butyl 2-(methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)amino)ethylcarbamate (100 mg, 0.26 mmol) to afford the desired product (100 mg, 78%) as a yellow solid: ESI MS m/z 494 [C₂₇H₃₁N₃O₄S+H]⁺.

Example 1310 (S)-9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, (S)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.20 mmol) was reacted with HCl in ether (10 mL) to afford the desired product (80 mg, 98%) as an off-white solid: ESI MS m/z 397 [C₂₂H₂₁FN₂O₂S+H]⁺.

Example 1253 9-(4-(1-Amino-3-methylbutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate (30 mg, 0.060 mmol) was reacted with HCl in ether (3 mL) to afford the desired product (22 mg, 97%) as an off-white solid; ¹H NMR (500 MHz, DMSO-d) δ 7.93 (s, 3H), 7.62 (d, J=5.4 Hz, 1H), 7.53 (d, J=9.1 Hz, 1H), 7.41 (d, J=9.0 Hz, 2H), 7.38-7.33 (m, 1H), 7.24 (d, J=8.2 Hz, 2H), 5.72 (d, J=5.4 Hz, 1H), 3.70 (s, 3H), 3.38-3.26 (m, 2H), 2.87 (dt, J=12.9, 6.3 Hz, 1H), 2.01 (dq, J=13.3, 6.6 Hz, 1H), 0.97 (t, J=7.8 Hz, 3H), 0.82 (t, J=9.9 Hz, 3H); ESI MS m/z 393 [C₂₃H₂₄N₂O₂S+H]⁺. HPLC 98.4% (AUC), t_(R)=11.65 min.

Example 555 9-(4-(1-Amino-3-methylbutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate (50 mg, 0.060 mmol) was reacted with HCl in ether (3 mL) to afford the desired product (37 mg, 92%) as an off-white solid: ESI MS m/1407 [C₂₄H₂₆N₂O₂S+H]⁺.

Example 1317 (R)-9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, (R)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (150 mg, 0.30 mmol) was reacted with HCl in ether (15 mL) to afford the desired product (105 mg, 81%) as an off-white solid: ¹H NMR (500 MHz, MeOD) δ 7.63 (dd, J=5.4, 2.4 Hz, 1H), 7.52 (dt, J=24.8, 7.8 Hz, 1H), 7.30 (s, 1H), 7.09 (m, 2H), 6.11 (dd, J=26.4, 5.4 Hz, 1H), 3.76 (s, 3H), 3.63-3.43 (m, 1H), 3.42-3.16 (m, 2H), 2.64 (s, 3H), 1.51 (d, J=7.0 Hz, 3H). ESI MS m/z 397 [C₂₂H₂₁FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=11.57 min.

Example 1316 (R)-9-(3-Fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, (R)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (50 mg, 0.10 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (35 mg, 85%) as an yellow solid; ¹H NMR (500 MHz, CD₃OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.53 (dt, J=28.7, 7.8 Hz, 1H), 7.29 (s, 1H), 7.17-7.04 (m, 2H), 6.10 (dd, J=31.6, 5.4 Hz, 1H), 3.75 (s, 3H), 3.68-3.24 (m, 3H), 2.78 (d, J=13.3 Hz, 3H), 2.64 (s, 3H), 1.52 (dd, J=7.0, 3.2 Hz, 3H); ESI MS m/z 411 [C₂₃H₂₃FN₂O₂S+H]⁺; HPLC 98.2% (AUC), t_(R)=11.79 min.

Example 1344 (R)-9-(4-(1-Aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (100 mg, 0.20 mmol) was reacted with HCl in ether (10 mL) to afford the desired product (75 mg, 94%) as an off-white solid: ESI MS m/z 393 [C₂₃H₂₄N₂O₂S+H]⁺.

Example 1273 9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (200 mg, 0.40 mmol) was reacted with HCl in ether (20 mL) to afford the desired product (145 mg, 91%) as an off-white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 10.80 (s, 1H), 8.06 (s, 3H), 7.74 (dd, J=14.6, 5.4 Hz, 1H), 7.52 (t, J=7.9 Hz, 1H), 7.30 (s, 1H), 7.16-7.02 (m, 2H), 5.87 (dd, J=43.2, 5.4 Hz, 1H), 3.70 (s, 3H), 3.51-3.40 (m, 1H), 3.26-3.07 (m, 2H), 2.59 (s, 3H), 1.39 (t, J=7.6 Hz, 3H); ESI MS m/z 397 [C₂₂H₂₁FN₂O₂S+H]⁺; HPLC 98.8% (AUC), t_(R)=11.60 min.

Example 1283 9-(4-(1-Amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, tert-butyl 2-(2-fluoro-4-(%-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate (52 mg, 0.10 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (25 mg, 59%) as an off-white solid; ¹H NMR (500 MHz, DMSO-d₆) δ 7.69 (dd, J=16.1, 5.4 Hz, 1H), 7.41 (dt, J=13.3, 8.0 Hz, 1H), 7.29 (d, J=3.4 Hz, 1H), 7.10-6.98 (m, 2H), 5.89-5.72 (m, 1H), 3.71 (t, J=6.8 Hz, 3H), 3.19-2.83 (m, 3H), 2.59 (s, 3H), 2.03 (dt, J=13.5, 6.7 Hz, 1H), 0.99 (t, J=10.0 Hz, 3H), 0.82 (dd, J=9.9, 6.8 Hz, 3H): ESI MS m/z 425 [C₂₄H₂₅FN₂O₂S+H]⁺; HPLC 93.4% (AUC), t_(R)=11.20 min.

Example 556 8-Methoxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutyl(methyl)carbamate (100 mg, 0.2 mmol) was reacted with HCl in ether (8 mL) to afford the desired product (40 mg, 47%) as an off-white solid: ESI MS m/z 421 [C₂₅H₂₈N₂O₂S+H]⁺

Example 1286 9-(3-Fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl carbamate (100 mg, 0.20 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (75 mg, 93%) as an off-white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 10.80 (s, 1H), 7.75 (dd, J=11.7, 5.4 Hz, 1H), 7.52 (t, J=7.8 Hz, 1H), 7.30 (s, 1H), 7.17-7.04 (m, 2H), 5.87 (dd, J=35.8, 5.4 Hz, 1H), 3.71 (s, 3H), 3.55 (dd, J=14.0, 6.8 Hz, 1H), 3.28 (m, 2H), 2.63 (d, J=5.5 Hz, 3H), 2.59 (s, 3H), 1.39 (dt, J=17.4, 7.6 Hz, 3H); ESI MS m/z 411 [C₂₃H₂₃FN₂O₂S+H]⁺; HPLC 98.9% (AUC), t_(R)=10.75 min.

Example 557 9-(3-Fluoro-4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutyl(methyl)carbamate (100 mg, 0.18 mmol) was reacted with HCl in ether (6 mL) to afford the desired product (55 mg, 70%) as an off-white solid: ESI MS m/z 439 [C₂₅H₂₇FN₂O₂S+H]⁺

Example 1317 (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, (R)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (510 mg, 1.1 mmol) was reacted with HCl in ether (25 mL) to afford the desired product (312 mg, 78%) as an off-white solid: ESI MS m/z 397 [C₂₂H₂₁FN₂O₂S+H]⁺

Example 1310 (S)-9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, (S)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (520 mg, 1.1 mmol) was reacted with HCl (25 ml) to afford desire product (300 mg, 74%) as an off-white solid: ¹H NMR (500 MHz, MeOD) δ 7.63 (d, J=5.4 Hz, 1H), 7.51 (dt, J=23.5, 7.8 Hz, 1H), 7.29 (s, 1H), 7.14-7.02 (m, 2H), 6.16-6.05 (m, 1H), 3.76 (s, 3H), 3.54 (ddd, J=46.9, 14.5, 7.3 Hz, 1H), 3.43-3.20 (m, 2H), 1.51 (d, J=7.0 Hz, 3H); ESI MS m/z 397 [C₂₂H₂₁FN₂O₂S+H]⁺; HPLC 98.9% (AUC), t_(R)=10.75 min.

Example 1387 (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

To a solution of (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride (110 mg, 0.27 mmol)) in a 1:1 mixture of MeOH/THF (3 mL) was added paraformaldehyde (7.5 mg, 0.24 mmol) followed by NaCNBH₃ (70 mg 1.2 mmol) and stirred at rt for 16 h. The reaction mixture was quenched by the addition of 2 N NaHCO₃ (1 mL), eluted through an SCX ion-exchange column and converted to HCl salt using General Procedure D-2 (Scheme II) to obtain the desired product (67 mg, 60%) as a white solid: ESI MS m/z 425 [C₂₄H₂₅FN₂O₂S+H]⁺;

Example 558 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure C (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (2.5 g, 5.4 mmol) was reacted with TFA (10 mL) to afford the desired product (1.6 g, 81%) as an off-white solid: ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺

Example 1205 N-(1-Chloropropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

To a mixture of N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (140 mg, 0.30 mmol) and triphenylphosphine (160 mg, 0.62 mmol) in DMF/CCl₄ (1 mL/3 mL) was added NCS (41 mg, 0.31 mmol) and the reaction mixture was stirred at room temperature for 15 h. The reaction mixture was diluted with water (ca. 20 mL), and extracted with DCM (1×50 mL). The extract was washed with water (2×20 mL), brine (1×10 mL), dried over sodium sulfate, and evaporated under vacuum. The residue was purified by flash chromatography to afford the desired product (100 mg, 74%) as light yellow solid; ESI MS m/z 464 [C₂₁H₁₉ClN₂O₄S+H]⁺

Example 1239 9-(4-(2-Amino-1-cyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D, tert-butyl 2-cyclopentyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (50 mg, 0.10 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (29 mg, 69%) as an off-white solid: ESI MS m/z 419 [C25H₂₆N₂O₂S+H]⁺; ¹H NMR (500 MHz, DMSO-d₆) δ 7.59 (d, J=5.4 Hz, 1H), 7.59 (d, J=5.4 Hz, 1H), 7.54 (d, J=9.0 Hz, 1H), 7.54 (d, J=9.0 Hz, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.44-7.36 (m, 2H), 7.45-7.35 (m, 2H), 7.28-7.19 (m, 2H), 7.28-7.19 (m, 2H), 5.72 (d, J=5.4 Hz, 1H), 5.72 (d, J=5.4 Hz, 1H), 3.70 (s, 3H), 3.33-3.20 (m, 2H), 2.84 (td, J=9.2, 6.0 Hz, 1H), 2.20-2.03 (m, 1H), 1.98-1.84 (m, 1H), 1.76-1.35 (m, 5H), 1.28 (dq, J=18.0, 8.9 Hz, 1H), 1.18-1.02 (m, 1H). HPLC >99% (AUC), t_(R)=12.45 min.

Example 1301 8-Methoxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, tert-butyl 3-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)piperidine-1-carboxylate (50 mg, 0.10 mmol) was reacted with HCl in ether (2.5 mL) to afford the desired product (31 mg, 77%) as an off-white solid: ESI MS m/z 405 [C₂₄H₂₄N₂O₂S+H]⁺

Example 1396 9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D1, tert-butyl 2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methyl)amino)ethylcarbamate (100 mg, 0.20 mmol) was reacted with HCl in ether (10 mL) to afford the desired product (65 mg, 83%) as an off-white solid: ESI MS m/z 394 [C₂₂H₂₃N₃O₂S+H]⁺

Example 559 tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (600 mg, 1.9 mmol) was reacted with tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate (1.34 g, 3.87 mmol) to afford the desired product (340 mg, 39%) as a brown solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 560 (R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (300 mg, 0.97 mmol) was reacted with (R)-tert-butyl methyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate (520 mg, 1.45 mmol) to afford the desired product (120 mg, 27%) as a brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 561 tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.4 mmol) was reacted with tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamate (2.6 g, 7.3 mmol) to afford the desired product (1.1 g, 50%) as a brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 562 tert-butyl 2-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-on (3.0 g, 9.7 mmol) was reacted with tert-butyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (5.7 g, 14 mmol) to afford the desired product (2.7 g, 56%) as a brown solid: ESI MS m/z 499 [C₂₆H₂₇ClN₂O₄S+H]⁺.

Example 563 2-(4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (500 mg, 1.6 mmol) was reacted with 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (600 g, 2.2 mmol) to afford the desired product (350 mg, 62%) as a brown solid: ESI MS m/z 361 [C₂₁H₁₆N₂O₂S+H]⁺.

Example 564 tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.0 g, 6.4 mmol) was reacted with tert-butyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (3.6 g, 9.7 mmol) to afford the desired product (864 mg, 28%) as a brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 565 (R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (3.0 g, 9.7 mmol) was reacted with (R)-tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate (5.0 g, 14 mmol) to afford the desired product (2.0 g, 47%) as a brown solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 566 tert-Butyl 2-ethyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (120 mg, 0.39 mmol) was reacted with 2-ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butan-1-amine (220 mg, 0.58 mmol) to afford the desired product (50 mg, 27%) as a brown solid: ESI MS m/z 507 [C₂₉H₃₄N₂O₄S+H]⁺.

Example 567 tert-Butyl 2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.8 mmol) was reacted with tert-butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate (2.6 g, 7.3 mmol) to afford the desired product (1.5 g, 65%) as a brown solid: ESI MS m/z 469 [C₂₅H₂₅FN₂O₄S+H]⁺.

Example 568 (R)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.4 mmol) was reacted with (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (2.0 g, 6.4 mmol) to afford the desired product (1.4 g, 48%) as a brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 569 tert-Butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.2 g, 3.8 mmol) was reacted with tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (2.2 g, 5.8 mmol) to afford the desired product (905 mg, 51%) as a brown solid: ESI MS m/z 483 [C₂₆H₂₇FN₂O₄S+H]⁺.

Example 570 (R)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (700 mg, 2.3 mmol) was reacted with (R)-tert-butyl methyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate (1.3 g, 3.4 mmol) to afford the desired product (383 mg, 38%) as a yellow solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 571 tert-Butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5-1H)-one (2.0 g, 6.4 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate (3.4 g, 9.4 mmol) to afford the desired product (1.93 g, 65%) as a brown solid: ESI MS m/z 451 [(C₂₅H₂₆N₂O₄S+H]⁺.

Example 572 2-(4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.84 mmol) was reacted with 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (1.87 g, 7.26 mmol) to afford the desired product (1.45 g, 82%) as a brown solid: ESI MS m/z 361 [C₂₁H₁₆N₂O₂S+H]⁺.

Example 573 (R)-tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (3.0 g, 9.26 mmol) was reacted with (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (5.2 g, 13.89 mmol) to afford the desired product (1.60 g, 35%) as a brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 574 tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (800 mg, 4.84 mmol) was reacted with tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (1.5 g, 4.16 mmol) to afford the desired product (550 mg, 46%) as a brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 575 tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (200 mg, 0.62 mmol) was reacted with tert-butyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (350 mg, 0.93 mmol) to afford the desired product (95 mg, 62%) as a brown solid: ESI MS m/z 493 [C₂₈H₃₂N₂O₄S+H]⁺.

Example 576 tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (260 mg, 0.80 mmol) was reacted with tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamate (430 g, 1.2 mmol) to afford the desired product (212 mg, 55%) as a yellow oil: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 577 tert-Butyl 1-(4-(6-chloro-%-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure H, tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylethylcarbamate) (130 mg, 0.37 mmol) was reacted with NCS (64 mg, 0.48 mmol) to afford the desired product (58 mg, 32%) as a yellow solid. ESI MS m/z 485 [C₂₅H₂₅ClN₂O₄S+H]⁺.

Example 578 (S)-tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Following General Procedure H, ((S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate) (200 mg, 0.41 mmol) was reacted with NCS (68 mg, 0.50 mmol) to afford the desired product (130 mg, 61%) as a yellow solid: ESI MS m/z 513 [C₂₇H₂₉ClN₂O₄S+H]⁺.

Example 579 (S)-tert-Butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure H, (S)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (500 mg, 1.08 mmol) was reacted with NCS (175 mg, 1.29 mmol)) to afford the desired product (310 mg, 58%) as a yellow solid: ESI MS m/z 499 [C₂₆H₂₇ClN₂O₄S+H]⁺.

Example 580 tert-Butyl (1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate

Following General Procedure H, tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl phenyl)cyclopropyl)methylcarbamate (300 mg, 0.629 mmol) was reacted with NCS (85 mg, 0.629 mmol) to afford the desired product (250 mg, 78%) as a yellow solid: ESI MS m/z 511 [C₂₇H₂₇ClN₂O₄S+H]⁺.

Example 581 tert-Butyl 2-chloro-4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate

Following General Procedure H, tert-butyl 2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (127 mg, 0.26 mmol) was reacted with NCS (43 mg, 0.312 mmol) to afford the desired product (70 mg, 52%) as a yellow solid: ESI MS m/z 519 [C₂₅H₂₄Cl₂N₂O₄S+H]⁺.

Example 582 tert-Butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate

Following General Procedure H, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (100 mg, 0.21 mmol) in (DMF) was reacted with NCS (34 mg, 0.25 mmol) to afford the desired product (65 mg, 61%) as a yellow solid: ESI MS m/z 513 [C₂₇H₂₉ClN₂O₄S+H]⁺.

Example 583 tert-Butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate

Following General Procedure H, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate (200 mg, 0.43 mmol) in (DMF) was reacted with NCS (70 mg, 0.50 mmol) to afford the desired product (120 mg, 55%) as a yellow solid: ESI MS m/z 500 [C₂₆H₂₇ClN₂O₄S+H]⁺.

Example 584 (R)-tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure H, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (300 mg, 0.67 mmol) was reacted with NCS (110 mg, 0.87 mmol) to afford the desired product (27 mg, 11%) as a yellow solid: ESI MS m/z 485 [C₂₅H₂₅ClN₂O₄S+H]⁺.

Example 585 tert-Butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate

Following General Procedure H, tert-butyl 2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (300 mg, 0.64 mmol) was reacted with NCS (94 mg, 0.71 mmol) to afford the desired product (150 mg, 46%) as a yellow solid. ESI MS m/z 503 [C₂₅H₂₁ClFN₂O₄S+H]⁺.

Example 586 tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate

Following General Procedure H, tert-butyl 1-(4-(8-methoxy-4-oxo-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate (220 mg, 0.47 mmol) was reacted with NCS (69 mg, 0.52 mmol) to afford the desired product (60 mg, 26%) as a brown solid. ESI MS m/z 499 [C₂₆H₂₇ClN₂O₄S+H]⁺.

Example 1041 9-(4-(1-Aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (50 mg, 0.10 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 2 mL, 2 mmol) to afford the desired product (21 mg, 58%) as a light yellow solid (21 mg, 58%): ¹H NMR (500 MHz, CD₄OD) δ 7.65 (dt, J=5.2, 3.4 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.41 (dt, J=4.0, 2.6 Hz, 2H), 7.30 (s, 1H), 6.07 (d, J=: 5.4 Hz, 1H), 4.62 (q, J=6.8 Hz, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 371 [C₁₉H₁₅ClN₁O₂S+H]⁺; HPLC 97.8% (AUC), t_(R)=9.72 min.

Example 1052 (R)-8-Hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5)-one Hydrochloride

Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (120 mg, 0.25 mmol was treated with BBr₃ (1.0 M in CH₂Cl₂, 3 mL, 3 mmol) to afford the desired product (50 mg, 56%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.64 (ddd, J=7.1, 5.6, 2.3 Hz, 2H), 7.57 (d, J=5.4 Hz, 1H), 7.49-7.39 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.48 (q, J=7.0 Hz, 1H), 2.72 (s, 3H), 1.80 (d, J=6.9 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC 97.6% (AUC), t_(R)=7.82 min.

Example 1081 (R)-9-(4-(1-Aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (0.35 mg, 0.07 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 2 mL, 2 mmol) to afford the desired product (23 mg, 84%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.67-7.61 (m, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.44-7.39 (m, 2H), 7.30 (s, 1H), 6.07 (d, J=5.4 Hz, 1H), 4.62 (q, J=6.8 Hz, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 371 [C₁₉H₁₅ClN₂O₂S+H]⁺; HPLC 97.2% (AUC), t_(R)=9.58 min.

Example 1209 9-(4-(3-(Aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-ethyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butyl)butylcarbamate (20 mg, 0.05 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 3 mL, 3 mmol) to afford the desired product (7.0 mg, 36%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.63 (d, J=8.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.45-7.37 (m, 3H), 7.19 (dd, J=8.9, 2.2 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 3.29 (s, 2H), 1.97 (dt, J=14.6, 7.2 Hz, 4H), 0.93 (t, J=7.4 Hz, 6H). ESI MS m/z 393 [C₂₃H₂₄N₂O₂S+H]⁺; HPLC 99.6% (AUC), t_(R)=9.47 min.

Example 1213 9-(4-(2-Aminoethyl)-3-fluorophenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate (100 mg, 0.18 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 5 mL, 5 mmol) to afford the desired product as an off-white solid (24 mg, 30%): ¹H NMR (500 MHz, CD₃OD) δ 7.69 (d, J=5.4 Hz, 1H), 7.51 (t, J=7.7 Hz, 1H), 7.48 (s, 1H), 7.14 (d, J=9.0 Hz, 2H), 6.18 (d, J=5.4 Hz, 1H), 3.37-3.20 (m, 3H), 3.14-3.04 (m, 1H); ESI MS m/z 433 [C₁₉H₁₄BrFN₂O₂S+H]⁺; HPLC 98.6% (AUC), t_(R)=9.12 min.

Example 1217 9-(4-(2-Aminoethyl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (78 mg, 0.16 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 3 mL, 3 mmol) to afford the desired product as a yellow solid (16 mg, 27%): ¹H NMR (500 MHz, CD₃OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.49 (t, J=7.9 Hz, 1H), 7.14-7.05 (m, 3H), 6.21 (d, J=5.4 Hz, 1H), 3.36-3.21 (m, 2H), 3.13-3.04 (m, 1H), 2.57 (s, 3H); ESI MS m/z 369 [C₂₀H₁₇FN₂O₂S+H]⁺; HPLC 97.3% (AUC), t_(R)=8.47 min.

Example 1166 (R)-9-(4(1-Aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (R)-tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.20 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 5 mL, 5 mmol) to afford the desired product as a white solid (23 mg, 30%): ¹H NMR (500 MHz, CD₃OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.56 (dd, J=7.9, 1.9 Hz, 1H), 7.47 (dd, J=7.8, 1.9 Hz, 1H), 7.39-7.28 (m, 3H), 6.12 (d, J=5.4 Hz, 1H), 3.36-3.13 (m, 3H), 1.49 (d, J=6.5 Hz, 3H); ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC 98.4% (AUC), t_(R)=9.19 min.

Example 1174 9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (120 mg, 0.25 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 5 mL, 5 mmol) to afford the desired product as an off-white solid (35 mg, 37%). ¹H NMR (500 MHz, CD₃OD) δ 7.65 (dd, J=5.4, 3.4 Hz, 1H), 7.59 (s, 1H), 7.51 (s, 1H), 7.43 (dd, J=8.9, 2.3 Hz, 1H), 7.24-7.09 (m, 2H), 6.22 (dd, J=9.4, 5.4 Hz, 1H), 3.62 (d, J=7.2 Hz, 1H), 3.49-3.25 (m, 2H), 1.52 (t, J=6.7 Hz, 3H); ESI MS m/z 369 [C₂₀H₁₇FN₂O₂S+H]⁺; HPLC 99.3% (AUC), t_(R)=8.37 min.

Example 1187 (R)-8-Hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (250 mg, 0.52 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 4 mL, 4 mmol) to afford the desired product as an light yellow solid (39 mg, 42%). ¹H NMR (500 MHz, CD₃OD) δ 7.58 (dd, J=10.8, 3.6 Hz, 2H), 7.50-7.46 (m, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.38 (dd, J=7.9, 1.8 Hz, 1H), 7.32 (dd, J=7.7, 1.7 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.14 (d, J=5.4 Hz, 1H), 3.37-3.28 (m, 3H), 2.75 (s, 3H), 1.50 (d, J=6.7 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 97.1% (AUC), t_(R)=8.43 min.

Example 1190 9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-e]quinolin-9-yl)phenyl)propylcarbamate (120 mg, 0.25 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 5 mL, 5 mmol) to afford the desired product as an off-white solid (39 mg, 42%). ¹H NMR (500 MHz, CD₃OD) δ 7.64 (dd, J=5.4, 4.6 Hz, 1H), 7.57 (t, J=7.8 Hz, 1H), 7.48 (t, J=7.8 Hz, 1H), 7.22-7.05 (m, 3H), 6.23 (dd, J=8.4, 5.4 Hz, 1H), 3.61 (dd, J=14.4, 7.2 Hz, 1H), 3.51-3.23 (m, 2H), 2.57 (s, 3H), 1.52 (t, J=7.0 Hz, 3H); ESI MS m/z 383 [C₂₁H₁₉FN₂O₂S+H]⁺; HPLC 96.1% (AUC), t_(R)=8.85 min.

Example 1133 9-(4-(2-Aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride

Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (79 mg, 0.25 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 9 mL, 9 mmol) to afford the desired product as a yellow solid (12 mg, 20%). ¹H NMR (500 MHz, CD₃OD) δ 7.61 (d, J=5.4 Hz, 1H), 7.49 (d, J=8.1 Hz, 2H), 7.31 (d, J=7.0 Hz, 3H), 6.10 (d, J=5.4 Hz, 1H), 3.37-3.27 (m, 2H), 3.12 (t, J=7.6 Hz, 2H); ESI MS m/z 371 [C₁₉H₁₅ClN₂O₂S+H]⁺; HPLC 96.9% (AUC), t_(R)=8.83 min.

Example 1142 9-(4-(2-Aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (410 mg, 0.76 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 10 mL, 10 mmol) to afford the desired product as an off-white solid (58 mg, 18%): ¹H NMR (500 MHz, CD₃OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.53-7.45 (m, 3H), 7.31 (d, J=8.1 Hz, 2H), 6.10 (d, J=5.4 Hz, 1H), 3.31-3.28 (m, 2H), 3.11 (t, J=7.6 Hz, 2H); ESI MS m/z 415 [C₁₉H₁₅BrN₂O₂S+H]⁺; HPLC 94.9% (AUC), t_(R)=9.02 min.

Example 1176 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (60 mg, 0.11 mmol) was reacted with BBr₃ (1.0 M in CH₂Cl₂, 6 mL, 6 mmol) to afford the desired product as an off-white solid (24 mg, 51%): ¹HNMR (500 MHz, CD₃OD) δ 7.64 (d, J=5.4 Hz, 1H), 7.56 (dd, J=7.9, 1.9 Hz, 1H), 7.50-7.45 (m, 2H), 7.37 (dd, J=7.9, 1.8 Hz, 1H), 7.32 (dd, J=7.7, 1.7 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.36-3.18 (m, 3H), 1.49 (d, J=6.5 Hz, 3H): ESI MS m/z 429 [C₂₀H₁₇BrN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.30 min.

Example 1136 9-(4-(1-Aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (40 mg, 0.08 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 3 mL, 3 mmol) to afford the desired product as an yellow solid (13 mg, 40%): ¹H NMR (500 MHz, CD₃OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.56 (dd, J=7.9, 1.8 Hz, 1H), 7.48 (dd, J=7.8, 1.8 Hz, 1H), 7.40-7.28 (m, 3H), 6.12 (d, J=5.4 Hz, 1H), 3.29-3.19 (m, 3H), 1.49 (d, J=6.3 Hz, 3H); ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC 99% (AUC), t_(R)=8.12 min.

Example 1132 (R)-6-Chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (R)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (43 mg, 0.09 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 4 mL, 4 mmol) to afford the desired product as a white solid (15 mg, 45%): ¹H NMR (500 MHz, CD₃OD) δ 7.69-7.59 (m, 3H), 7.45 (ddd, J=7.0, 5.8, 2.1 Hz, 2H), 7.30 (s, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.48 (q, J=6.9 Hz, 1H), 2.72 (s, 3H), 1.79 (d, J=6.9 Hz, 3H); ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC 97.1% (AUC), t_(R)=8.85 min.

Example 1219 9-(4-(2-Aminoethyl)-3-fluorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate (70 mg, 0.14 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 6 mL, 6 mmol) to afford the desired product as a white solid (26 mg, 48%); ¹H NMR (500 MHz, CD₃OD) δ 7.67 (d, J=5.4 Hz, 1H), 7.51 (t, J=7.7 Hz, 1H), 7.30 (s, 1H), 7.17-7.11 (m, 2H), 6.18 (d, J=5.4 Hz, 1H), 3.35-3.20 (m, 2H), 3.14-3.04 (m, 1H); ESI MS m/z 389 [C₁₉H₁₄ClFN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.93 min.

Example 1228 9-(4-(1-Amino-2-methylpropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (40 mg, 0.08 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 4 mL, 4 mmol) to afford the desired product as a brown solid (21 mg, 67%); ¹H NMR (500 MHz, CD₃OD) δ 7.64 (d, J=8.4 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.36 (d, J=8.3 Hz, 2H), 7.09 (s, 1H), 6.18 (d, J=5.4 Hz, 1H), 3.28 (s, 2H), 2.58 (s, 3H), 1.58 (s, 6H): ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC 96.5% (AUC), t_(R)=9.04 min.

Example 1242 9-(4-(2-Aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate (90 mg, 0.19 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 8 mL, 8 mmol) to afford the desired product as a light brown solid (25 mg, 53%): ¹H NMR (500 MHz, CD₃OD) δ 7.57 (d, J=5.4 Hz, 1H), 7.45 (dd, J=20.6, 7.8 Hz, 2H), 7.32-7.26 (m, 2H), 7.09 (s, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.65 (dd, J=13.7, 6.9 Hz, 1H), 3.14-2.99 (m, 2H), 2.57 (s, 3H), 1.41 (d, J=6.6 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 98.6% (AUC), t_(R)=8.68 min.

Example 1191 9-(4-(2-Aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (30 mg, 0.06 mmol was treated with BBr₃ (1.0 M in CH₂Cl₂, 4 mL, 4 mmol) to afford the desired product as a light yellow solid (20 mg, 90%): ¹H NMR (500 MHz, CD₃OD) δ 7.55 (d, J=5.4 Hz, 1H), 7.47 (d, J=8.1 Hz, 2H), 7.30 (d, J=8.1 Hz, 2H), 7.07 (d, J=0.8 Hz, 1H), 6.14 (d, J=5.4 Hz, 1H), 3.34-3.27 (m, 2H), 3.11 (t, J=7.5 Hz, 2H), 2.57 (s, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC 98.4% (AUC), t_(R)=8.32 min.

Example 1364 8-Hydroxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 8-methoxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one (32 mg, 0.06 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 3 mL, 3 mmol) to afford the desired product as a light yellow solid (15 mg, 62%): ¹H NMR (500 MHz, CD₃OD) δ 7.55 (d, J=5.4 Hz, 1H), 7.47 (d, J=8.1 Hz, 2H), 7.34-7.27 (m, 2H), 7.07 (d, J=0.7 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.39 (t, J=7.6 Hz, 2H), 3.18-3.10 (m, 2H), 2.79 (s, 3H), 2.57 (s, 3H); ESI MS m/z 365 [(C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.41 min.

Example 1307 (R)-8-Hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrobromide

Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (2.08 g, 4.23 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 40 mL, 40 mmol) to afford the desired product as a yellow solid (1.05 g, 65%); ¹H NMR (500 MHz, CD₃OD) δ 7.60-7.54 (m, 2H), 7.46 (dd, J=7.8, 1.9 Hz, 1H), 7.37 (dd, J=7.9, 1.8 Hz, 1H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (d, J=0.8 Hz, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.37-3.24 (m, 3H), 2.74 (s, 3H), 2.57 (s, 3H), 1.50 (d, J=6.8 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.74 min.

Example 1169 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrobromide

Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (2.20 g, 4.60 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 50 mL, 50 mmol) to afford the desired product as a yellow solid (1.50 g, 73%): ¹H NMR (500 MHz, CD₃OD) δ 7.58 (d, J=5.4 Hz, 1H), 7.55 (dd, J=7.9, 1.8 Hz, 1H), 7.45 (dd, J=7.8, 1.9 Hz, 1H), 7.35 (dd, J=7.9, 1.7 Hz, 1H), 7.30 (dd, J=7.7, 1.6 Hz, 1H), 7.08 (d, J=0.8 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 3.36-3.19 (m, 3H), 2.57 (d, J=0.6 Hz, 3H), 1.50 (d, J=6.4 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 98.3% (AUC), t_(R)=8.64 min.

Example 587 tert-Butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate

Following General Procedure I, tert-butyl 2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (1.1 g, 2.3 mmol) was reacted with NBS (540 mg, 3.1 mmol) to afford the desired product (920 mg, 70%) as a brown solid. ESI MS m/z 547 [C₂₅H₂₄BrFN₂O₄S+H]⁺.

Example 588 tert-Butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate

Following General Procedure I, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (600 mg, 1.3 mmol) was reacted with NBS (330 mg, 1.9 mmol) to afford the desired product (350 mg, 51%) as a yellow solid: ESI MS m/z 557 [C₂₇H₂₉BrN₂O₄S+H]⁺.

Example 589 tert-Butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenyl)propylcarbamate

Following General Procedure I, tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (500 mg, 1.0 mmol) was reacted with NBS (220 mg, 1.2 mmol) to afford the desired product (280 mg, 48%) as a brown oil. ESI MS m/z 561 [C₂₆H₂₆BrFN₂O₄S+H]⁺.

Example 590 tert-Butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate

Following General Procedure I, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (600 mg, 1.3 mmol) was reacted with NBS (280 mg, 1.5 mmol) to afford the desired product (410 mg, 60%) as a reddish brown solid. ESI MS m/z 529 [C₂₅H₂₅BrN₂O₄S H]⁺.

Example 59 (R)-tert-Butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure I, (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (220 mg, 0.39 mmol) was reacted with NBS (90 mg, 0.51 mmol) to afford the desired product (60 mg, 28%) as a reddish oil: ESI MS m/z 543 [C₂₆H₂₇BrN₂O₄S+H]⁺.

Example 592 tert-Butyl 2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate

Following General Procedure I, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate (300 mg, 0.55 mmol) was reacted with trimethylboroxine (207 mg, 1.65 mmol) and Pd(pph₃)₄ (63 mg, 0.05 mmol) to afford the desired product (155 mg, 58%) as a brown solid. ESI MS m/z 483 [C₂₆H₂₇FN₂O₄S+H]⁺.

Example 593 tert-Butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure I, tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenyl)propylcarbamate (282 mg, 0.50 mmol) was reacted with trimethylboroxine (170 mg, 1.35 mmol) and Pd(pph₃)₄ (50 mg, 0.04 mmol) to afford the desired product (130 mg, 52%) as a yellow solid. ESI MS m/z 497 [C₂₇H₂₉FN₂O₄S+H]⁺.

Example 1216 9-(4-(2-Aminoethyl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, tert-butyl 2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (50 mg, 0.10 mmol) was reacted with TFA (2 mL) to afford the desired product (32 mg, 80%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.48 (dd, J=9.7, 6.1 Hz, 1H), 7.29 (s, 1H), 7.08 (ddd, J=9.0, 6.2, 1.6 Hz, 2H), 6.12 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.34-3.27 (m, 1H), 3.27-3.06 (m, 3H), 2.64 (s, 3H); ESI MS m/z 383 [C₂₁H₁₉FN₂O₂S+H]⁺; HPLC 97.6% (AUC), t_(R)=9.22 min.

Example 1161 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (200 mg, 0.55 mmol) was reacted with TFA (10 mL) to afford the desired product (51 mg, 26%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.61-7.44 (m, 4H), 7.39 (d, J=9.1 Hz, 1H), 7.30 (ddd, J=13.2, 7.9, 1.7 Hz, 2H), 6.00 (d, J=5.4 Hz, 1H), 3.33-3.18 (m, 3H), 1.49 (d, J=6.6 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 97.6% (AUC), t_(R)=8.88 min

Example 1305 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (1.5 g, 3.1 mmol) was reacted with TFA (30 mL) to afford the desired product (520 mg, 47%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.56 (d, J=5.4 Hz, 1H), 7.50 (dd, J=7.8, 1.8 Hz, 1H), 7.45 (dd, J=7.7, 1.9 Hz, 1H), 7.28 (ddd, J=9.4, 7.0, 1.7 Hz, 3H), 6.01 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.36-3.18 (m, 3H), 2.64 (s, 3H), 1.48 (d, J=6.6 Hz, 3H); ESI MS m/z 379 [C₂₂H₁₂N₂O₂S+H]⁺; HPLC 99% (AUC), t_(R)=8.81 min.

Example 1201 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, (R)-tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (60 mg, 0.12 mmol) was reacted with TFA (4 mL) to afford the desired product (28 mg, 52%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.61 (d, J=5.4 Hz, 1H), 7.54-7.50 (m, 2H), 7.48 (dd, J=7.8, 1.7 Hz, 1H), 7.32-7.25 (m, 2H), 5.97 (d, J=5.4 Hz, 1H), 3.76 (s, 1H), 3.29-3.17 (m, 3H), 1.48 (d, J=6.5 Hz, 2H); ESI MS m/z 399 [C₂₁H₁₉ClN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.65 min.

Example 1298 (R)-8-Methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (600 mg, 1.2 mmol) was reacted with TFA (20 mL) to afford the desired product (330 mg, 69%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.56 (d, J=5.4 Hz, 1H), 7.52 (dd, J=7.9, 1.9 Hz, 1H), 7.47 (dd, J=7.7, 1.9 Hz, 1H), 7.28 (ddd, J=14.7, 7.9, 1.7 Hz, 3H), 6.00 (d, J=5.4 Hz, 1H), 3.36-3.26 (m, 3H), 2.76 (s, 3H), 2.64 (s, 3H), 1.48 (d, J=6.7 Hz, 3H); ESI MS m/z 393 [(C₂₃H₂₄N₂O₂S+H]⁺; HPLC 98.6% (AUC), t_(R)=8.96 min.

Example 594 (R)-tert-Butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure H, (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylpropylcarbamate (400 mg, 0.86 mmol) was reacted with NCS (138 mg, 1.03 mmol) to afford the desired product (210 mg, 49%) as a brown solid. ESI MS m/z 499 [C₂₆H₂₇ClN₂O₄S+H]⁺.

Example 595 tert-Butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate

Following General Procedure 1H, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (200 mg, 0.43 mmol) was reacted with NCS (68 mg, 0.52 mmol) to afford the desired product (79 mg, 38%) as a brown solid. ESI MS m/z 485 [C₂₅H₂₅ClN₂O₄S+H]⁺.

Example 596 tert-Butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure H, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (180 mg, 0.39 mmol) was reacted with NCS (57 mg, 0.42 mmol) to afford the desired product (110 mg, 56%) as a yellowish solid. ESI MS m/z 499 [C₂₆H₂₇ClN₂O₄S+H]⁺.

Example 597 (R)-tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate

Following General Procedure H, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (200 mg, 0.43 mmol) was reacted with NCS (69 mg, 0.52 mmol) to afford the desired product (43 mg, 20%) as a yellowish solid. ESI MS m/z 499 [C₂₆H₂₇ClN₂O₄S+H]⁺.

Example 598 tert-Butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethylcarbamate

Following General Procedure H, tert-butyl 2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (300 mg, 0.64 mmol) was reacted with NCS (94 mg, 0.71 mmol) to afford the desired product (150 mg, 46%) as a yellow solid. ESI MS m/z 503 [C₂₅H₂₄ClFN₂O₄S+H]⁺.

Example 373 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

To a solution of 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile (1.4 g, 4.0 mmol) in toluene (10 mL) at 0° C. was added BH₃.THF (1.0 M in THF, 10 mL, 10 mmol) and the reaction was warmed to room temperature and heated at reflux for 4 h. The reaction was quenched by adding methanol (1 mL) at 0° C. The resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product (352 mg, 24%) as a brown solid: ESI MS m/z 365 [CH₂₁H₂₀N₂O₂S+H]⁺.

Example 1112 9-(4-(1-(Dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 1387, 9-(4-(1-aminopropan-2-yl)phenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (15 mg, 0.040 mmol) was reacted with paraformaldehyde (4.0 mg, 0.13 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (12 mg, 75%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.66-7.51 (m, 3H), 7.47-7.30 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.67-3.57 (m, 1H), 3.51-3.38 (m, 2H), 2.95 (d, J=16.0 Hz, 6H), 1.49 (d, J=6.5 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.46 min.

Example 1126 (R)-6-Chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 1387, (R)-9-(4-(1-aminoethyl)phenyl-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (120 mg, 0.32 mmol) was reacted with paraformaldehyde (29 mg, 0.97 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (21 mg, 16%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.71 (dd, J=10.5, 7.8 Hz, 2H), 7.64 (d, J=5.4 Hz, 1H), 7.47 (t, J=7.1 Hz, 2H), 7.31 (s, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.66 (q, J=6.9 Hz, 1H), 2.97 (s, 3H), 2.86 (s, 3H), 1.86 (d, J=7.0 Hz, 3H). ESI MS m/z 399 [C₂₁H₁₉ClN₂O₂S+H]⁺; HPLC 97.5% (AUC), t_(R)=9.96 min.

Example 1188 (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 1387, (R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one hydrochloride (40 mg, 0.11 mmol) was reacted with paraformaldehyde (7 mg, 0.21 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (28 mg, 67%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.65-7.52 (m, 3H), 7.44-7.32 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.62 (d, J=3.1 Hz, 1H), 3.46 (dd, J=13.2, 4.7 Hz, 2H), 2.97 (s, 3H), 2.94 (s, 3H), 1.49 (d, J=6.6 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.57 min.

Example 1193 9-(4-(1-(Dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 1387, 9-(4-(1-Aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride (30 mg, 0.08 mmol) was reacted with paraformaldehyde (9 mg, 0.31 mmol) and after purification the resulting material was converted to the Hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (25 mg, 75(%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.67-7.51 (m, 2H), 7.26-7.10 (m, 2H), 7.08 (dd, J=1.6, 0.8 Hz, 1H), 6.20 (dd, J=8.1, 5.4 Hz, 1H), 3.88-3.40 (m, 3H), 3.0-2.96 (m, 6H), 2.57 (s, 3H), 1.57-1.46 (m, 3H); ESI MS m/z 411 [C₂₃H₂₃FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.14 min.

Example 1347 (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 1387, (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (30 mg, 0.10 mmol) was reacted with paraformaldehyde (6 mg, 0.20 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (12 mg, 29%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.66-7.57 (m, 2H), 7.55 (d, J=7.8 Hz, 1H), 7.40-7.27 (m, 3H), 6.07 (d, J=5.4 Hz, 1H), 3.62 (dd, J=12.2, 8.9 Hz, 1H), 3.46 (ddd, J=11.7, 9.3, 6.3 Hz, 2H), 2.98 (s, 3H), 2.94 (s, 3H), 1.48 (d, J=6.5 Hz, 3H); ESI MS m/z 413 [C₂₂H₂₁ClN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.46 min.

Example 1379 (R)-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 1387, ((R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one hydrochloride (15 mg, 0.04 mmol) was reacted with acetaldehyde (5 uL, 0.08 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (8 mg, 50%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.66-7.49 (m, 3H), 7.42-7.27 (m, 2H), 7.08 (s, 1H), 6.13 (dd, J=19.9, 5.4 Hz, 1H), 3.70 (dd, J=12.8, 10.3 Hz, 1H), 3.58-3.14 (m, 4H), 2.91 (d, J=23.4 Hz, 3H), 2.57 (s, 3H), 1.49 (dd, J=6.8, 3.3 Hz, 3H), 1.36 (dt, J=12.8, 7.3 Hz, 3H); ESI MS m/z 407 [C₂₄H₁₁N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.16 min.

Example 1324 (R)-9-(4-(1-(Dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 1387, (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrobromide (100 mg, 0.26 mmol) was reacted with paraformaldehyde (24 mg, 0.80 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (34 mg, 34%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.61-7.55 (m, 1H), 7.53 (dd, J=7.8, 1.8 Hz, 1H), 7.36 (dd, J=7.9, 1.7 Hz, 1H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (s, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.61 (dd, J=12.3, 9.3 Hz, 1H), 3.45 (dt, J=9.1, 6.2 Hz, 2H), 2.97 (s, 1H), 2.94 (s, 1H), 2.57 (s, 1H), 1.48 (d, J=6.6 Hz, 1H); ESI MS m/z 393 [C₂₃H₂₄N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.90 min.

Example 1306 (R)-8-Hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D-3, (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one hydrobromide (120 mg, 0.26 mmol) was dissolved in aqueous HCl (100 mmol) and stirred concentrated at room temperature for 2 h, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt. The desired product was dried under high vacuum to afford the desired product as a light yellow solid (27 mg, 28%): ¹H NMR (500 M Hz, CD₃OD) δ 7.61-7.53 (m, 2H), 7.46 (dd, J=7.8, 1.8 Hz, 1H), 7.36 (dd, J=7.9, 1.6 Hz, 1H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (s, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.41-3.24 (m, 3H), 2.74 (s, 3H), 2.57 (s, 3H), 1.50 (d, J=6.8 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC 98.7% (AUC), t_(R)=8.82 min.

Example 408 N-tert-Butyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (5.0 g, 16 mmol) was reacted with 4-(N-tert-butylsulfamoyl)phenylboronic acid (5.4 g, 21 mmol) to afford the desired product (4.3 g, 60%) as a yellow solid: ESI MS m/z [C₂₂H₂₂N₂O₄S₂+H]⁺.

Example 409 9-(1H-Indazol-6-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.32 mmol) was reacted with 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (120 mg, 0.48 mmol) to afford the desired product (35 mg, 31%) as brown solid: ESI MS m/z 348 [C₁₈H₁₁N₃O₂S+H]⁺.

Example 169 9-[4-(2-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure C, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (310 mg, 0.69 mmol) was reacted with TFA (2 mL) to afford the desired product (220 mg, 90%) as an off-white solid: ¹H NMR (500 MHz, DMSO-d) δ 7.91 (s, 1H), 7.91 (br s, 2H), 7.71 (d, J=5.4 Hz, 1H), 7.52 (d, J=9.1 Hz, 1H), 7.40 (m, 3H), 7.22 (d, J=8.1 Hz, 2H), 5.80 (d, J=5.4 Hz, 1H), 3.68 (s, 3H), 3.20-3.17 (m, 2H), 3.02-2.99 (m, 2H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC 98.8% (AUC), t_(R)=8.32 min.

Example 145 9-(4-{3-[2-(Diethylamino)ethylamino]propoxy}phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.33 mmol) was reacted with N′,N′-diethyl-N²-{3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propyl}ethane-1,2-diamine (250 mg, 0.67 mmol) to afford the desired product (58 mg, 37%) as a brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.56 (d, J=5.4 Hz, 1H), 7.52 (d, J=9.1 Hz, 1H), 7.36 (d, J=9.1 Hz, 1H), 7.18 (d, J=8.6 Hz, 2H), 7.12 (d, J=8.6 Hz, 2H), 6.11 (d, J=5.4 Hz, 1H), 4.25 (t, J=5.7 Hz, 2H), 3.74 (s, 3H), 3.74-3.43 (m, 4H), 3.42 (t, J=7.4 Hz, 2H), 3.34-3.33 (m, 4H), 2.35-2.25 (m, 2H), 1.37 (t, J=7.3 Hz, 6H); ESI MS m/z 480 [C₂₇H₃₃N₃O₃S+H]⁺; HPLC 98.6%, t_(R)=8.42 min.

Example 410 tert-Butyl 4-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]piperazine-1-carboxylate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (80 mg, 0.26 mmol) was reacted with tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate (170 mg, 0.44 mmol) to afford the desired product (68 mg, 32%) as a yellow solid: ESI MS m/z 492 [C₂₇H₂₉N₃O₄S+H]⁺.

Example 411 8-Methoxy-9-[4-(piperazin-1-yl)phenyl]thieno[2,3-c]quinolin-4(5H)-one

Following General Procedure C, tert-butyl 4-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]piperazine-1-carboxylate (160 mg, 0.33 mmol) was reacted with TFA (4 mL) to afford the desired product (23 mg, 22%) as a light yellow solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.84 (s, 1H), 8.72 (s, 2H), 7.76 (d, J=5.4 Hz, 1H), 7.49 (d, J=9.0 Hz, 1H), 7.37 (d, J=9.1 Hz, 1H), 7.20-7.03 (m, 4H), 5.95 (d, J=5.4 Hz, 1H), 3.68 (s, 3H), 3.52-3.41 (m, 4H), 3.31 (s, 4H).

Example 412 8-Methoxy-9-{4-[4-(methylsulfonyl)piperazin-1-yl]phenyl}thieno[2,3-c]quinolin-4(5H)-one

To a solution of 8-methoxy-9-[4-(piperazin-1-yl)phenyl]thieno[2,3-c]quinolin-4(5H)-one (89 mg, 0.23 mmol) in methylene chloride (2 mL) was added N,N-diisopropylethylamine (0.42 mL, 0.68 mmol) and methanesulfonyl chloride (45 μL, 0.27 mmol) and the reaction mixture was stirred for 1 h. The reaction mixture was quenched with water and the layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over Na₂SO₄, filtered, concentrated and the residue was purified by preparatory HPLC (C18 silica, acetonitrile/water w/0.05% TFA gradient) to afford the desired product (72 mg, 68%) as a brown solid: ESI MS m/z 470 [C₂₃H₂₃N₃O₄S₂+H]⁺.

Example 413 tert-Butyl 4-(8-Methoxy-2-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Following General Procedure B A, 9-bromo-8-methoxy-2-methylthieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.31 mmol) was reacted with 4-[(tert-butoxycarbonylamino)methyl]phenylboronic acid (120 mg, 0.40 mmol) to afford desired product (80 mg, 55%) as a brown solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 414 N-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]methanesulfonamide

Following Step 1 from General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (50 mg, 0.10 mmol) was reacted with 4-(methylsulfonamido)phenylboronic acid (52 mg, 0.24 mmol) to afford the desired product (40 mg, 62%) as a brown solid: ESI MS m/z 400 [C₁₉H₁₆N₂O₄S₂+H]⁺.

Example 415 tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (600 mg, 2.0 mmol) was reacted with tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (340 mg, 39%) as a brown solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 416 8-Methoxy-9-{4-[1-(piperidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 4-[1-(piperidin-1-yl)ethyl]phenylboronic acid (170 mg, 0.73 mmol) to afford the desired product (10 mg, 5%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.74-7.66 (m, 2H), 7.62-7.53 (m, 2H), 7.49-7.34 (m, 3H), 5.94 (d, J=5.4 Hz, 1H), 4.61 (q, J=6.9 Hz, 1H), 3.86-3.78 (m, 1H), 3.76 (s, 1H), 3.47 (d, J=12.6 Hz, 1H), 3.10-2.98 (m, 1H), 2.96-2.82 (m, 1H), 2.11-1.91 (m, 2H), 1.89 (d, J=7.0 Hz, 2H), 1.85-1.70 (m, 1H).

Example 417 2-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (350 mg, 1.1 mmol) was reacted with 2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile (440 mg, 1.7 mmol) to afford the desired product (400 mg, >99%) as a brown solid: ESI MS m/z 365 [C₂₀H₁₃FN₂O₂S+H]⁺.

Example 265 9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

To a solution of 2-[2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile (49 mg, 0.14 mmol) in toluene (3 mL) was added borane (1.0 M in THF, 3.0 mL, 0.30 mmol) and the reaction was stirred at reflux for 3 h. The reaction mixture was cooled to room temperature, concentrated and the residue was purified by preparatory HPLC. The residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the hydrochloride salt (4.5 mg, 9%) as a brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.50 (t, J=7.8 Hz, 1H), 7.40 (d, J=9.1 Hz, 1H), 7.11-7.05 (m, 2H), 6.11 (d, J=5.4 Hz, 1H), 3.76 (s, 3H), 3.25-3.08 (m, 4H), 2.75 (br s, 3H); ESI MS m/z 369 [C₂₀H₁₇FN₂O₂S+H]⁺; HPLC 95.0% (AUC), t_(R)=7.89 min.

Example 418 (S)-tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (280 mg, 0.89 mmol) was reacted with (S)-tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (320 mg, 1.1 mmol) to afford the desired product (220 mg, 55%) as a white solid: ESI MS m/z 351 [C₂₅H₂₆N₂O₄S-Boc]⁺.

Example 232 (S)-9-[4-(1-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, (S)-tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (90 mg, 0.12 mmol) was reacted with TFA (3 mL) to afford the desired product (11 mg, 15%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.65-7.62 (m, 2H), 7.56-7.54 (m, 2H), 7.40-7.38 (m, 3H), 6.04 (d, J=5.5 Hz, 1H), 4.62 (q, J=7.0 Hz, 1H), 7.73 (s, 3H), 1.77 (d, J=6.9 Hz, 3H); ESI MS m/z 351[C₂₀H₁₈N₂O₂S+H]⁺; HPLC 97.6% (AUC), t_(R)=8.33 min.

Example 216 8-Methoxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (120 mg, 0.39 mmol) was reacted with 4-[1-(pyrrolidin-1-yl)ethyl]phenylboronic acid (170 mg, 0.77 mmol) to afford the desired product (70 mg, 45%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.69-7.67 (m, 2H), 7.60 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.44-7.40 (m, 3H), 5.96 (d, J=5.4 Hz, 1H), 4.54 (q, J=6.8 Hz, 1H), 3.89-3.84 (m, 1H), 3.76 (s, 3H), 3.38-3.16 (m, 3H), 2.29-2.00 (m, 4H), 1.87 (d, J=6.9 Hz, 3H); ESI MS m/z 405 [C₂₄H₂₄N₂O₂S+H]⁺; HPLC >99%, t_(R)=8.98 min.

Example 419 8-Methoxy-9-{4-[1-(piperidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 4-[1-(piperidin-1-yl)ethyl]phenylboronic acid (170 mg, 0.73 mmol) to afford the desired product (10 mg, 5%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.74-7.66 (m, 2H), 7.62-7.53 (m, 2H), 7.49-7.34 (m, 3H), 5.94 (d, J=5.4 Hz, 1H), 4.61 (q, J=6.9 Hz, 1H), 3.86-3.78 (m, 1H), 3.76 (s, 1H), 3.47 (d, J=12.6 Hz, 1H), 3.10-2.98 (m, 1H), 2.96-2.82 (m, 1H), 2.11-1.91 (m, 2H), 1.89 (d, J=7.0 Hz, 2H), 1.85-1.70 (m, 1H).

Example 420 2-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile

Following Step 1 from General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (350 mg, 1.1 mmol) was reacted with 2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile (440 mg, 1.7 mmol) to afford the desired product (400 mg, >99%) as a brown solid: ESI MS m/z 365 [C₂₀H₁₃FN₂O₂S+H]⁺.

Example 421 9-[4-(3-Aminopropyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following the procedure outlined for Example 265, 3-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile (250 mg, 0.69 mmol) was reacted with borane (1.0 M in THF, 10 mL, 10 mmol) to afford the desired product (150 mg, 60%) as a brown oil: ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺.

Example 274 (R)-9-[4-(1-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, (R)-tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (50 mg, 0.11 mmol) was reacted with TFA (3 mL) to afford the desired product (11 mg, 26%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.63-7.62 (m, 2H), 7.56-7.55 (m, 2H), 7.40-7.37 (m, 3H), 6.04 (d, J=5.4 Hz, 1H), 4.62 (q, J=6.9 Hz, 1H), 3.79 (s, 3H), 2.77 (br s, 3H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC 98.7% (AUC), t_(R)=8.24 min.

Example 422 (R)-tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate

Following Step 1 from General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (480 mg, 1.5 mmol) was reacted with (R)-tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (800 mg, 2.3 mmol) to afford the desired product (410 mg, 59%) as a brown solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 423 2-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]-2-methylpropanenitrile

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (380 mg, 1.2 mmol) was reacted with 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile (500 mg, 1.9 mmol) to afford the desired product (260 mg, 56%) as a brown solid: ESI MS m/z 375 [C₂₂H₁₈N₂O₂S+H]⁺.

Example 424 9-[4-(1-Amino-2-methylpropa-2-yl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following the procedure outlined for Example 265, 2-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]-2-methylpropanenitrile (250 mg, 0.67 mmol) was reacted with borane (1.0 M in THF, 10 mL, 10.0 mmol) to afford the desired product (100 mg, 40%) as a yellow solid: ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺.

Example 425 9-{3-Fluoro-4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (180 mg, 0.58 mmol) was reacted with 1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]pyrrolidin-3-ol (280 mg, 0.87 mmol) to afford the desired product (130 mg, 48%) as a brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.79-7.72 (m, 1H), 7.66 (d, J=5.4 Hz, 1H), 7.58 (d, J=9.1 Hz, 1H), 7.42 (d, J=9.1 Hz, 1H), 7.33-7.21 (m, 2H), 6.09 (td, J=5.3, 2.4 Hz, 1H), 4.75-4.53 (m, 3H), 3.91-3.66 (m, 4H), 3.66-3.34 (m, 3H), 2.55-2.44 (m, 1H), 2.28-2.15 (m, 1H), 2.14-2.04 (m, 1H).

Example 426 tert-Butyl 5-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2,3-dihydro-1H-inden-2-ylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.1 g, 3.6 mmol) was reacted with tert-butyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate (2.0 g, 5.6 mmol) to afford the desired product (250 mg, 15%) as a brown solid: ESI MS m/z 363 [C₂₆H₂₆N₂O₄S+H-100]⁺.

Example 427 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile

Following General Procedure B, 1-(4-bromophenyl)cyclopropanecarbonitrile (1.5 g, 7.1 mmol) was reacted with bis(pinacolato)diboron (2.7 g, 10 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.3 g, 4.2 mmol) to afford the desired product (378 mg, 29%) as a white solid: ESI MS m/z 373 [C₂₂H₁₆N₂O₂S+H]⁺.

Example 428 tert-Butyl 7-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1 g, 3.3 mmol) was reacted with tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.8 g, 5.0 mmol) to afford the desired product (720 mg, 48%) as a brown solid: ESI MS m/z 463 [C₂₆H₂₆N₂O₄S+H]⁺.

Example 429 8-Methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one

Following General Procedure C, tert-Butyl 7-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (260 mg, 0.53 mmol) was reacted with TFA (5 mL) afford the desired product (180 mg, 20%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.61-7.56 (m, 1H), 7.55 (dd, J=9.0, 3.2 Hz, 1H), 7.44 (d, J=7.8 Hz, 1H), 7.41-7.36 (m, 1H), 7.22 (d, J=7.8 Hz, 1H), 7.16 (s, 1H), 6.13 (d, J=5.4 Hz, 1H), 4.42 (s, 2H), 3.73 (s, 3H), 3.68-3.54 (m, 2H), 3.29-3.20 (m, 2H).

Example 430 tert-Butyl 1-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (800 mg, 2.6 mmoL) was reacted with tert-butyl 1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (1.4 g, 3.9 mmol) to afford the desired product (480 mg, 40%) as a brown solid: ESI MS m/z 469 [C₂₅H₂FN₂O₄S+H]⁺.

Example 431 3-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (400 mg, 1.3 mmol) was reacted with 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile (600 mg, 1.9 mmol) to afford the desired product (320 mg, 69%) as a brown solid: ESI MS m/z 361 [C₂₁H₁₆N₂O₂S+H]⁺.

Example 432 9-(4-Acetylphenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.0 g, 3.2 mmol) was reacted with 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (1.2 g, 4.8 mmol) to afford the desired product (520 mg, 46%) as a brown solid: ¹H NMR (500 MHz, CD₃OD) δ 8.16 (d, J=8.1 Hz, 2H), 7.61-7.54 (m, 2H), 7.45-7.39 (m, 3H), 6.05 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 2.71 (s, 3H).

Example 433 9-{4-[1-(Cyclopentylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure E, N-[1-(4-bromophenyl)ethyl]cyclopentanamine (600 mg, 2.3 mmol) was reacted with bis(pinacolato)diboron (410 mg, 1.6 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (250 mg, 0.81 mmol) to afford the desired product (330 mg, 97%) as a brown solid: ¹H NMR (300 MHz, CD₃OD) δ 7.73-7.64 (m, 2H), 7.60-7.50 (m, 2H), 7.47-7.34 (m, 3H), 6.01 (d, J=5.4 Hz, 1H), 4.57 (q, J=6.8 Hz, 1H), 3.74 (s, 3H), 3.62-3.45 (m, 1H), 2.30-2.02 (m, 2H), 1.93-1.85 (m, 2H), 1.81 (d, J=6.7 Hz, 3H), 1.77-1.51 (m, 4H).

Example 434 tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.1 g, 3.7 mmol) was reacted with tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propylcarbamate (2.0 g, 5.5 mmol) to afford the desired product (1.2 g, 68%) as a white solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 337 9-[4-(1-Aminopropyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propylcarbamate (30 mg, 0.064 mmol) was reacted with TFA (2 mL) to afford the desired product (17 mg, 72%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.64-7.57 (m, 2H), 7.54 (d, J=2.0 Hz, 1H), 7.53 (d, J=1.6 Hz, 1H), 7.39-7.35 (m, 3H), 5.98 (d, J=5.4 Hz, 1H), 4.32 (q, J=5.1 Hz, 1H), 5.53 (s, 3H), 2.17-2.07 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.47 min.

Example 435 (S)-tert-Butyl 1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (760 mg, 2.4 mmol) was reacted with (S)-tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate (1.3 g, 3.7 mmol) to afford the desired product (730 mg, 66%) as a light yellow solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 436 9-{4-[1-(Dimethylamino)ethyl]-phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.8 mmol) was reacted with 4-[1-(dimethylamino)ethyl]phenylboronic acid (1.5 g, 6.3 mmol) to afford the desired product (1.1 g, 58%) as a white solid: ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺.

Example 139 tert-Butyl {1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]piperidin-4-yl}methylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (110 mg, 0.31 mmol) was reacted with 4-({4-[(tert-butoxycarbonylamino)methyl]piperidin-1-yl}methyl)phenylboronic acid (80 mg, 0.26 mol) to afford the desired product (25 mg, 20%) as a yellow glass: ¹H NMR (500 MHz, CD₃OD) δ 7.69-7.66 (m, 2H), 7.57-7.54 (m, 2H), 7.41-7.38 (m, 3H), 5.96-5.95 (m, 1H), 4.48-4.44 (m, 2H), 3.75 (s, 3H), 3.70-3.64 (m, 2H), 3.27-2.91 (m, 4H), 2.25-1.95 (m, 2H), 1.57 (s, 1H), 1.52-1.42 (m, 10H); ESI MS m/z 534 [C₃₀H₃₅N₃O₄S+H]⁺; HPLC 97.6% (AUC), t_(R)=14.10 min.

Example 437 (E)-tert-Butyl 1-[3-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl]piperidin-4-ylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (180 mg, 0.48 mmol) was reacted with (E)-tert-butyl 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-4-ylcarbamate (100 mg, 0.32 mmol) to afford the desired product (86 mg, 57%) as a brown solid: ESI MS m/z 470 [C₂₅H₃₁N₃O₄S+H]⁺.

Example 152 (E)-9-[3-(4-Aminopiperidin-1-yl)prop-1-enyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure C, (E)-tert-butyl 1-[3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl]piperidin-4-ylcarbamate (40 mg, 0.085 mmol) was reacted with TFA (1 mL) to afford the desired product (15 mg, 86%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.94 (d, J=5.3 Hz, 1H), 7.86 (d, J=5.3 Hz, 1H), 7.34 (d, J=9.1 Hz, 1H), 7.24 (d, J=9.1 Hz, 1H), 7.06 (d, J=16.0 Hz, 1H), 6.14-6.08 (m, 1H), 4.12 (d, J=7.1 Hz, 2H), 3.84 (br s, 2H), 3.55 (br s, 1H), 3.26 (br s, 3H), 2.38 (d, J=13.3 Hz, 2H), 2.12-2.07 (m, 2H), 1.35-1.31 (m, 1H), 0.96-0.90 (m, 1H); ESI MS m/z 370 [C₂₀H₂₃N₃O₂S+H]⁺; HPLC 95.6% (AUC), t_(R)=6.78 min.

Example 164 9-{4-[(Dimethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following the procedure outlined for Example 460, 9-[4-(aminomethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.27 mmol) was reacted with formaldehyde (37% in water, 20 mg, 0.67 mmol) to afford the desired product (45 mg, 47%): ¹H NMR (500 MHz, CD₃OD) δ 7.67 (d, J=8.2 Hz, 2H), 7.58-7.54 (m, 2H), 7.42-7.38 (m, 3H), 5.96 (d, J=5.5 Hz, 1H), 4.47 (s, 2H), 3.75 (s, 3H), 2.98 (s, 6H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.50 min.

Example 438 9-{4-[(Diethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure E, N-(4-bromobenzyl)-N-ethylethanamine (200 mg, 0.83 mmol) was reacted with bis(pinacolato)diboron (230 mg, 0.91 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (260 mg, 0.83 mmol) to afford the desired product (58 mg, 25%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.69 (d, J=8.2 Hz, 2H), 7.60-7.54 (m, 2H), 7.46-7.43 (m, 2H), 7.41 (d, J=9.1 Hz, 1H), 5.99 (d, J=5.4 Hz, 1H), 4.50 (s, 2H), 3.75 (s, 3H), 3.41-3.32 (m, 4H), 1.44 (t, J=7.3 Hz, 6H).

Example 188 8-Methoxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one

Following General Procedure E, 1-(4-bromophenyl)-N-methylmethanamine (200 mg, 1.0 mmol) was reacted to bis(pinacoato)diboron (280 mg, 1.1 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (310 mg, 1.0 mmol) to afford the desired product (145 mg, 42%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.65 (d, J=8.1 Hz, 2H), 7.58-7.52 (m, 2H), 7.42-7.35 (m, 3H), 6.02 (d, J=5.4 Hz, 1H), 4.33 (s, 2H), 3.73 (s, 3H), 2.83 (s, 3H).

Example 439 tert-Butyl 4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 4-[(tert-butoxycarbonylamino)methyl]phenylboronic acid (180 mg, 0.73 mmol) to afford the desired product (180 mg, 83%) as a brown solid: ESI MS m/z 437 [C₂₄H₂₄N₂O₄S+H]⁺.

Example 440 9-{4-[(Isopropylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure E, N-(4-bromobenzyl)propan-2-amine (200 mg, 0.88 mmol) was reacted with bis(pinacolato)diboron (240 mg, 0.96 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (270 mg, 0.88 mmol) to afford the desired product (190 mg, 57%) as a light brown solid: ¹H NMR (500 MHz, CD₃CD₂OD) δ 7.68-7.63 (m, 2H), 7.56-7.49 (m, 2H), 7.41-7.34 (m, 3H), 6.04 (dd, J=5.4, 2.4 Hz, 1H), 4.33 (s, 2H), 3.72-3.67 (m, 3H), 3.56-3.50 (m, 1H), 1.45 (dd, J=6.6, 2.2 Hz, 6H).

Example 269 9-{4-[(Ethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure E, N-(4-bromobenzyl)ethanamine (300 mg, 1.4 mmol) was reacted with bis(pinacolato)diboron (390 mg, 1.5 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (430 mg, 1.4 mmol) to afford the desired product (160 mg, 31%) as a brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.67 (d, J=8.1 Hz, 2H), 7.57-7.54 (m, 2H), 7.39-7.36 (m, 3H), 6.03 (d, J=5.5 Hz, 1H), 4.34 (s, 2H), 3.72 (s, 3H), 3.23 (q, J=7.3 Hz, 2H), 1.97 (s, 2H), 1.42 (t, J=7.3 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.61 min.

Example 441 (E)-tert-Butyl 1-[3-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl]piperidin-3-ylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (530 mg, 1.7 mmol) was reacted with (E)-tert-Butyl 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-3-ylcarbamate (320 mg, 0.88 mmol) to afford the desired product (190 mg, 47%) as a light brown solid: ESI MS m/z 456 [C₂₄H₂₉N₃O₄S+H]⁺.

Example 442 tert-Butyl 4-(6-Fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Following General Procedure B, 9-bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.50 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (200 mg, 0.60 mmol) to afford the desired product (100 mg, 48%) as a brown solid: ESI MS m/z 455 [C₂₄H₂₃FN₂O₄S+H]⁺.

Example 257 9-[4-(Aminomethyl)phenyl]-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure D-1, tert-butyl 4-(6-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (15 mg, 0.030 mmol) was reacted with HCl (2 N in diethyl ether, 1.5 mL) to afford the desired product (10 mg, 90%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.63 (d, J=8.1 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.36 (d, J=8.1 Hz, 2H), 7.32 (d, J=12.7 Hz, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.27 (s, 2H), 3.72 (s, 3H); ESI MS m/z 355 [C₁₉H₁₅FN₂O₂S+H]⁺; HPLC 99% (AUC), t_(R)=10.64 min.

Example 443 9-{4-[1-(Dimethylamino)ethyl]phenyl})-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.40 mmol) was reacted with 4-[1-(dimethylamino)ethyl]phenylboronic acid (120 mg, 0.50 mmol) to afford the desired product (55 mg, 35%) as an off-white solid: ESI MS m/z 415 [C₂₂H₂₀F₂N₂O₂S+H]⁺.

Example 444 9-{4-[2-(Dimethylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following the procedure outlined for Example 460, 9-[4-(2-aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with formaldehyde (100 mg, 1.0 mmol) to afford the desired product (85 mg, 84%) as a white solid: ¹H NMR (500 MHz, CD₃CN+D₂O) δ 7.54-7.50 (m, 2H), 7.42 (d, J=7.8 Hz, 2H), 7.32 (d, J=9.1 Hz, 1H), 7.13 (d, 7.8 Hz, 2H), 5.83 (d, J=5.3 Hz, 1H), 3.69 (s, 3H), 3.43-3.40 (m, 2H), 3.16-3.13 (m, 2H), 2.92 (s, 6H).

Example 445 9-(4-Amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (150 mg, 0.50 mmol) to afford the desired product (64 mg, 60%) as a brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.61 (d, J=5.3 Hz, 1H), 7.58-7.53 (m, 2H), 7.41 (d, J=5.3 Hz, 1H), 7.16 (s, 1H), 7.01 (d, J=5.3 Hz, 1H), 6.09 (d, J=5.1 Hz, 1H), 3.93 (s, 3H), 3.77 (s, 3H).

Example 222 9-{4-[1-(Dimethylamino)ethyl]phenyl}-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure B, 9-bromo-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with 4-[1-(dimethylamino)ethyl]phenylboronic acid (100 mg, 0.45 mmol) to afford the desired product (49 mg, 41%) as a white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 10.28 (s, 1H), 7.77 (d, J=5.4 Hz, 1H), 7.71 (q, J=8.0 Hz, 2H), 7.46 (d, J=12.8 Hz, 1H), 7.38 (d, J=8.2 Hz, 2H), 5.69 (d, J=5.4 Hz, 1H), 4.64 (t, J=6.0 Hz, 1H), 3.71 (s, 3H), 2.82 (d, J=4.2 Hz, 3H), 2.70 (d, J=4.4 Hz, 3H), 1.74 (d, J=6.8 Hz, 3H); ESI MS m/z 397 [C₂₂H₂₁FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.85 min.

Example 446 tert-Butyl{(1-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]piperidin-4-yl}methylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with tert-butyl{1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]piperidin-4-yl}methylcarbamate (150 mg, 0.36 mmol) to afford the desired product (81 mg, 49% 0 was a yellow solid: ESI MS m/z 552 [C₃₀H₃₄FN₃O₄S+H]⁺.

Example 447 tert-Butyl[5-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)thiophen-2-yl]methylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (150 mg, 0.48 mmol) was reacted with 5-[(tert-butoxycarbonylamino)methyl]thiophen-2-ylboronic acid (130 mg, 0.53 mmol) to afford the desired product (30 mg, 18%) as a off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.74 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.1 Hz, 1H), 7.36 (d, J=9.1 Hz, 1H), 6.49 (d, J=3.1 Hz, 1H), 6.40 (br s, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.27 (s, 2H), 3.82 (s, 3H), 1.39 (s, 9H).

Example 448 2-Fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

Following General Procedure E, 4-bromo-2-fluoro-N-(2-hydroxyethyl)benzenesulfonamide (3.30 mg, 1.1 mmol) was reacted with bis(pinacolato)diborane (300 mg, 1.2 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (310 mg, 1.0 mmol) to afford the desired product (68 mg, 13%) as an off-white solid: ¹H NMR (300 MHz, DMSO-d₆) δ 11.95 (s, 1H), 8.04 (t, J=5.8 Hz, 1H), 7.93 (t, J=7.8 Hz, 1H), 7.93 (d, J=5.4 Hz, 1H), 7.57 (d, J=9.1 Hz, 1H), 7.49-7.43 (m, 2H), 7.30 (dd, J=8.0, 1.5 Hz, 1H), 5.89 (d, J=5.4 Hz, 1H), 4.78 (t, J=5.6 Hz, 1H), 3.72 (s, 3H), 3.46 (q, J=6.2 Hz, 2H), 3.05 (m, 2H).

Example 449 4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.32 mmol) was reacted with N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (110 mg, 0.35 mmol) to afford the desired product (33 mg, crude) as a brown solid: ESI MS m/z 415 [C₂₀H₈N₂O₄S₂+H]⁺.

Example 450 N-(2-Hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (500 mg, 1.5 mmol) was reacted with N-(2-hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (450 mg, 1.5 mmol) to afford the desired product (130 mg, 20%) as an off-white solid: ¹H NMR (300 MHz, DMSO-d₆) δ 11.93 (s, 1H), 7.94 (d, J=8.4 Hz, 2H), 7.78-7.74 (m, 2H), 7.58-7.42 (m, 4H), 5.74 (d, J=5.4 Hz, 1H), 4.78 (t, J=5.6 Hz, 1H), 3.71 (s, 3H), 3.45 (q, J=6.1 Hz, 2H), 2.93 (q, J=6.2 Hz, 2H).

Example 333 N-(2-Fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

To a solution of N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (120 mg, 0.28 mmol) in methylene chloride (10 mL) and THF (6 mL) under nitrogen at −78° C. was added DAST (89 mg, 0.56 mmol) and the reaction mixture was stirred at −78° C. for 2 h and warmed to room temperature and stirred for 16 h. The reaction mixture was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate/hexanes gradient). The resulting crude residue was triturated in methylene chloride and filtered to afford the desired product (90 mg, 75%) as a off-white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.92 (s, 1H), 8.10 (t, J=5.9 Hz, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.76 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.1 Hz, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.43 (d, J=9.2 Hz, 1H), 5.75 (d, J=5.4 Hz, 1H), 4.51 (t, J=4.9 Hz, 1H), 4.42 (t, J=4.9 Hz, 1H), 3.71 (s, 3H), 3.24 (q, J=5.2 Hz, 1H), 3.19 (q, J=5.2 Hz, 1H); ESI MS m/z 433 [C₂₀H₁₇FN₂O₄S₂+H]⁺; HPLC 93.4% (AUC), t_(R)=15.64 min.

Example 451 tert-Butyl 4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Following General Procedure E, tert-butyl 4-bromobenzylcarbamate (2.9 g, 10 mmol) was reacted with bis(pinacolato)diborane (2.8 g, 11 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.8 g, 9.0 mmol) to afford the desired product (2.7 g, 68%) as a brown solid: ESI MS m/z 437 [C₂₄H₂₄N₂O₄S+H]⁺.

Example 452 tert-Butyl 4-(6-Bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

To a solution of tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (29 mg, 0.055 mmol) in DMF (1 mL) was added N-bromosuccinimide (12 mg, 0.066 mmol) and the reaction was stirred at room temperature for 1 h and heated at 50° C. for 2 h. The reaction mixture was concentrated and the residue was purified by preparatory TLC (silica, methanol/methylene chloride gradient) to afford the desired product (10 mg, 35%): ESI MS m/z 516 [C₂₄H₂₃BrN₂O₄S+H]⁺.

Example 453 tert-Butyl 2-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate

Following General Procedure E, tert-butyl 2-(4-bromophenyl)propan-2-ylcarbamate (160 mg, 0.50 mmol) was reacted with bis(pinacolato)diboron (140 mg, 0.55 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (140 mg, 0.45 mmol) to afford the desired product (110 mg, 47%) as a brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 454 tert-Butyl 4-(6-Chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

A solution of tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (45 mg, 0.10 mmol) and N-chlorosuccinimide (17 mg, 0.13 mmol) in DMF (1 mL) was heated at 50° C. for 3 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by preparatory HPLC (water/acetonitrile w 0.05% TFA gradient) to afford the desired product (15 mg, 32%) as a brown solid: ESI MS m/z 471 [C₂₄H₂₃ClN₂O₄S+H]⁺.

Example 455 tert-Butyl 2-[4-(6-Chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate

A solution of tert-butyl 2-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate (130 mg, 0.27 mmol) and N-chlorosuccinimide (47 mg, 0.35 mmol) in DMF (3 mL) was heated at 70° C. for 2 h. The reaction mixture was cooled to room temperature, quenched with water and the aqueous layer was extracted with methylene chloride/methanol (9:1). The combined organic layers were dried over sodium sulfate, filtered, concentrated and the residue was purified by column chromatography (silica, methanol/methylene chloride gradient) to afford the desired product (42 mg, 31%) as a brown solid: ESI MS m/z 500 [C₂₆H₂₇ClN₂O₄S+H]⁺.

Example 456 N-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl]methanesulfonamide

Following General Procedure E, N-(4-bromo-2-methylphenyl)methanesulfonamide (130 mg, 0.50 mmol) was reacted with bis(pinacolato)diboron (140 mg, 0.55 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (140 mg, 0.45 mmol) to afford the desired product (51 mg, 27%) as a brown solid: ESI MS m/z 415 [C₂₀H₁₈N₂O₄S₂+H]⁺.

Example 599 (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure E, (R)-tert-butyl 2-(4-bromophenyl)propylcarbamate (60 mg, 0.20 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (60 mg, 0.20 mmol) to afford the desired product (52 mg, 62%) as a brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S]⁺

Example 600 tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate

Following General Procedure E, tert-butyl 2-(4-bromophenyl)propan-2-ylcarbamate (0.44 g, 1.4 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (0.45 g, 1.4 mmol) to afford the desired product (0.53 g, 79%) as a brown solid: ESI MS m/z 479 [C₂₇H₃₀N₂O₄S+H]⁺.

Example 601 tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Following General Procedure E, tert-butyl 4-bromobenzylcarbamate (0.78 g, 2.7 mmol) was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (0.76 g, 2.5 mmol) to afford the desired product (0.66 g, 62%) as a brown solid: ESI MS m/z 437 [C₂₄H₂₄N₂O₄S+H]⁺.

Example 602 (R)-tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure E, (R1-tert-butyl 1-(4-bromophenyl)ethylcarbamate (60 mg, 0.20 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (60 mg, 0.20 mmol) to afford the desired product (52 mg, 62%) as a brown solid:

Example 603 (R)-tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure E, (R1-tert-butyl 1-(4-bromophenyl)ethylcarbamate (1.5 g, 5 mmol) was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.4 g, 4.6 mmol) to afford the desired product (0.90 g, 43%) as a brown solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 604 (S)-tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure E, (S)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (60 mg, 0.20 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (60 mg, 0.20 mmol) to afford the desired product (52 mg, 62%) as a brown solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 605 tert-Butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure E, tert-butyl 1-(4-bromophenyl)ethylcarbamate (3.0 g, 10 mmol) was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (2.8 g, 9.0 mmol) to afford the desired product (2.0 g, 50%) as a brown solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 606 (R)-tert-Butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure H, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (0.67 g, 1.5 mmol) was reacted with N-chlorosuccinimide (0.29 g, 1.6 mmol) in DMF (10 mL) to afford the desired product (0.28 g, 35%) as a brown solid: ESI MS m/z 499 [C₂₆H₂₇ClN₂O₄S+H]⁺.

Example 607 tert-Butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure I, tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (1.0 g, 2.2 mmol) was reacted with N-bromosuccinimide (0.45 g, 2.5 mmol) in DMF (10 mL) to afford the desired product (0.35 g, 29%) as a brown solid: ESI MS m/z 529 [C₂₅H₂₅BrN₂O₄S+H]⁺.

Example 608 tert-Butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Following General Procedure I, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (0.66 g, 1.5 mmol) was reacted with N-bromosuccinimide (0.30 g, 1.7 mmol) in DMF (10 mL) to afford the desired product (0.39 g, 51%) as a brown solid: ESI MS m/z 515 [C₂₄H₂₃BrN₂O₄S+H]⁺.

Example 609 tert-Butyl 4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Following General Procedure J, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (52 mg, 0.10 mmol) was reacted with trimethylboroxine (13 mg, 0.10 mmol) to afford the desired product (43 mg, 95%) as a grey solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 610 tert-Butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

Following General Procedure J, tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (32 mg, 0.060 mmol) was reacted with trimethylboroxine (8 mg, 0.060 mmol) to afford the desired product (20 mg, 61%) as a grey solid: ESI MS m/z 465 [C₂₆H₂₈N₂O₄S+H]⁺.

Example 1168 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (43 mg, 0.095 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (18 mg, 51%) as a grey solid: ¹H NMR (300 MHz, DMSO-d₆) δ 10.75-10.65 (m, 1H), 9.14 (s, 1H), 8.09 (s, 3H), 7.68 (d, J=5.4 Hz, 1H), 7.43 (d, J=8.4 Hz, 2H), 7.21 (d, J=8.3 Hz, 2H), 7.05 (s, 1H), 5.86 (d, J=5.4 Hz, 1H), 3.27-2.95 (m, 3H), 1.38 (d, J=6.6 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 98.6%, t_(R)=8.42 min.

Example 1122 (R)-9-(4-(1-Aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (43 mg, 0.095 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (18 mg, 51%) as a grey solid: ¹H NMR (300 MHz, DMSO-d₆) δ 10.72 (s, 1H), 8.52 (s, 3H), 7.65 (dd, J=13.3, 6.8 Hz, 3H), 7.30 (d, J=8.2 Hz, 2H), 7.06 (s, 1H), 5.87 (d, J=5.4 Hz, 1H), 4.64-4.45 (m, 1H), 2.50 (s, 3H), 1.63 (d, J=6.8 Hz, 3H); ESI MS m/z 480 [C₂₇H₃₃N₃O₃S+H]⁺; HPLC 98.6%, t_(R)=8.42 min.

Example 1212 9-(4-(Aminomethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (43 mg, 0.095 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (18 mg, 51%) as a grey solid: ¹H NMR (500 MHz, CD₃OD) δ 7.62 (d, J=8.1 Hz, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.39 (d, J=8.0 Hz, 2H), 7.07 (s, 1H), 6.10 (d, J=5.4 Hz, 1H), 4.26 (s, 1H), 2.57 (s, 3H); ESI MS m/z 335 [C₁₉H₁₆N₂O₂S−H]⁻; HPLC 96.7%, t_(R)=7.99 min.

Example 1225 (S)-9-(4-(1-Aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (52 mg, 0.11 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (20 mg, 46%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.62 (d, J=7.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.39 (d, J=7.4 Hz, 2H), 7.07 (s, 1H), 6.09 (d, J=5.4 Hz, 1H), 4.61 (q, J=6.9 Hz, 1H), 2.57 (s, 3H), 1.76 (d, J=6.9 Hz, 3H): ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC >99%, t_(R)=8.40 min.

Example 1032 9-(4-(1-Aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride

Following General Procedure F, tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl ethylcarbamate (17 mg, 0.032 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (8 mg, 55%) as a light yellow solid: 1H NMR (500 MHz, MeOD) δ 7.62 (d, J=7.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.42-7.37 (m, 2H), 7.07 (d, J=0.7 Hz, 1H), 6.09 (d, J=5.4 Hz, 1H), 4.67-4.56 (m, 1H), 2.57 (s, 3H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 415 [C₁₉H₁₅BrN₂O₂S+H]⁺; HPLC 95.0%, t_(R)=12.16 min.

Example 1066 9-(4-(1-Aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (20 mg, 0.043 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (10 mg, 60%) as a light grey solid: ¹H NMR (500 MHz, MeOD) δ 7.62 (d, J=7.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.42-7.37 (m, 2H), 7.07 (d, J=0.7 Hz, 1H), 6.09 (d, J=5.4 Hz, 1H), 4.67-4.56 (m, 1H), 2.57 (s, 3H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC >99%, t_(R)=8.40 min.

Example 1123 (R)-9-(4-(1-Aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, (R)-tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl phenyl)ethylcarbamate (24 mg, 0.045 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (18 mg, 88%) as a light grey solid: ¹H NMR (500 MHz, MeOD) δ 7.64 (dd, J=10.4, 3.5 Hz, 31H), 7.61 (d, J=5.4 Hz, 1H), 7.47 (s, 1H), 7.42 (d, J=7.5 Hz, 2H), 6.07 (d, J=5.4 Hz, 1H), 4.65-4.59 (m, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 415 [C₁₉H₁₅BrN₂O₂S+H]⁺; HPLC 97.0%, t_(R)=8.74 min.

Example 1159 (R)-9-(4-(1-Aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride

Following General Procedure F, (R)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (30 mg, 0.063 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (22 mg, 87%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.63-7.56 (m, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.40 (t, J=6.6 Hz, 3H), 7.08 (s, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.31 (dd, J=9.2, 5.9 Hz, 1H), 2.57 (s, 3H), 2.21-2.01 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 383 [C₂₀H₁₇ClN₂O₂S−H]⁻; HPLC 96.9%, t_(R)=8.69 min.

Example 1157 (R)-9-(4-(1-Aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride

Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (30 mg, 0.063 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (22 mg, 87%) as a light grey solid: ¹H NMR, (500 MHz, CD₃OD) δ 7.63-7.56 (m, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.40 (t, J=6.6 Hz, 3H), 7.08 (s, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.31 (dd, J=9.2, 5.9 Hz, 1H), 2.57 (s, 3H), 2.21-2.01 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99%, t_(R)=8.69 min.

Example 1330 9-(4-(2-Aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5)-one

Following General Procedure F, (S)-9-(4-(1-aminoethyl)phenyl-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (52 mg, 0.11 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (20 mg, 46%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.68 (d, J=8.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.41 (d, J=8.4 Hz, 2H), 7.07 (s, 1H), 6.08 (d, J=5.4 Hz, 1H), 2.57 (s, 3H), 1.86 (s, 6H); ESI MS m/z 363 [C₂₁H₂₀N₂O₂S−H]⁻; HPLC 98.7%, t_(R)=8.51 min.

Example 611 982 9-bromo-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one

To a suspension of 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (2.2 g, 6.8 mmol) in a mixture of DMF (15 mL) and THF (15 mL) at 0° C. was added sodium hydride (60%, 0.54 g, 13.6 mmol). The reaction mixture was stirred at 0° C. for 30 min before (2-(chloromethoxy)ethyl)trimethylsilane (3.4 g, 20 mmol) was added. The resulting mixture was stirred at rt overnight and then poured into ice-water (50 mL). The resulting precipitate was filtered and purified by column chromatography (silica, heptane/ethyl acetate) to afford the desired product (2.7 g, 87%) as a light yellow solid: ESI MS m/z 454 [C₁₉H₂₄BrNO₃SSi+H]⁺.

Example 612 9-Bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one

To a stirred solution of diidopropylamine (85 μL, 0.6 mmol) in THF (2.5 mL) at −78° C. was added n-BuLi (2.5 M, 0.24 mL, 0.60 mmol) and the reaction mixture was stirred at 0° C. for 10 min then cooled to −78° C. A solution of 9-bromo-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.23 g, 0.50 mmol) in THF (1 mL) was added dropwise and the reaction mixture was stirred at −78° C. for 30 min. Iodomethane (93 μL, 1.5 mmol) was added and the reaction mixture was stirred at −78° C. for 2 h and quenched by the addition of satd. aq. ammonium chloride and extracted with dichloromethane. The organics were dried over Na₂SO₄, filtered, concentrated in vacuo and the residue was purified by column chromatography (silica, heptane/ethyl acetate) to afford the desired product (0.13 g, 55%) as a white solid: ESI MS m/z 468 [C₂₀H₂₆BrNO₃SSi+H]⁺.

Example 613 (R)-tert-Butyl 2-(4-(8-methoxy-2,6-dimethyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (0.12 g, 0.33 mmol) was reacted with 9-bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.12 g, 0.33 mmol) to afford the desired product (78 mg, 45%) as a solid: ESI MS m/z 623 [C₃₄H₄₆N₂O₅SSi+H]⁺.

Example 1341 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one hydrochloride

To a solution of (R)-tert-butyl 2-(4-(8-methoxy-2,6-dimethyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (24 mg, 0.039 mmol) in CH₂Cl₂ (1 mL) at rt was added trifluoroacetic acid (1.0 mL) and the reaction was stirred at that temperature for 2 h. The mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH₄OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product (5 mg, 30%) as a hydrochloride salt: ¹H NMR (500 MHz, CD₃OD) δ 7.52 (dd, J=7.8, 1.5 Hz, 1H), 7.47 (dd, J=7.7, 1.5 Hz, 1H), 7.32 (s, 1H), 7.31-7.22 (m, 2H), 5.30 (d, J=2.7 Hz, 1.1H), 3.29-3.18 (m, 3H), 2.63 (s, 3H), 1.47 (d, J=6.1 Hz, 3H): ESI MS m/z 392 [C₂₃H₂₄N₂O₄S+H]⁺.

Example 1340 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-hydroxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one

To a solution of (R)-tert-butyl 2-(4-(8-methoxy-2,6-dimethyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (40 mg, 0.064 mmol) in CH₂C₂ (1 mL) at 0° C. was added BBr₃ (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) and the reaction was stirred at that temperature for 1 h and quenched by pouring onto water or ice-water. The resulting mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH₄OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt: ¹H NMR (500 MHz, CD₃OD) δ 7.55 (dd, J=7.9, 1.9 Hz, 1H), 7.45 (dd, J=7.7, 1.9 Hz, 1H), 7.34 (dd, J=7.9, 1.8 Hz, 1H), 7.28 (dd, J=7.7, 1.7 Hz, 1H), 7.06 (d, J=0.7 Hz, 1H), 5.70 (d, J=1.1 Hz, 1H), 3.29-3.13 (m, 3H), 2.55 (s, 3H), 2.30 (d, J=1.0 Hz, 3H), 1.50 (d, J=6.5 Hz, 3H); ESI MS m/z 378 [C₂₂H₂₂N₂O₂S+H]⁺.

Example 614 9-Bromo-2-chloro-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one

To a stirred solution of diidopropylamine (85 μL, 0.6 mmol) in THF (2.5 mL) at −78° C. was added n-BuLi (2.5M, 0.24 mL, 0.6 mmol). The resulting mixture was stirred at 0° C. for 10 min and then cooled at −78° C. A solution of 9-bromo-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thienio[2,3-c]quinolin-4(5H)-one (0.23 g, 0.50 mmol) in T-IF (1 mL) was added dropwise and the resulting mixture was stirred at −78° C. for 30 min. Hexachloroethane (0.24 g, 1.0 mmol) was added dropwise and the mixture was stirred at −78° C. for 2 h and allowed to warm to rt. The reaction was quenched by adding saturated ammonium chloride and extracted with dichloromethane (2×). The combined extracts were dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was purified by column chromatography (heptane/ethyl acetate) to afford the desired product (0.13 g, 52%) as a white solid: ESI MS m/z 488 [C₁₉H₂₃BrClNO₃SSi+H]⁺.

Example 615 (R)-tert-Butyl 2-(4-(2-chloro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure E, (R)-tert-butyl 2-(4-bromophenyl)propylcarbamate (97 mg, 0.31 mmol) was reacted with 9-bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.10 g, 0.21 mmol) to afford the desired product (62 mg, 46%) as a solid: ESI MS m/z 643 [C₃₃H₄₃ClN₂O₅SSi+H]⁺.

Example 1354 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-2-chloro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride

To a solution of (R)-tert-butyl 2-(4-(2-chloro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (11 mg, 0.017 mmol) in CH₂Cl₂ (1 mL) at rt was added trifluoroacetic acid (1.0 mL) and the reaction was stirred at that temperature for 2 h. The mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH₄OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product (7 mg, 92%) as a hydrochloride salt: ¹H NMR (500 MHz, CD₃OD) δ 7.52 (dd, J=7.8, 1.5 Hz, 1H), 7.47 (dd, J=7.7, 1.5 Hz, 1H), 7.32 (s, 1H), 7.31-7.22 (m, 2H), 5.30 (d, J=2.7 Hz, 1H), 3.29-3.18 (m, 3H), 2.63 (s, 3H), 1.47 (d, J=6.1 Hz, 3H); ESI MS m/z 413 [C₂₂H₂₁ClN₂O₂S I H]⁺.

Example 1353 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-2-chloro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride

To a solution of (R)-tert-butyl 2-(4-(2-chloro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (32 mg, 0.050 mmol) in CH₂Cl₂ at 0° C. was added BBr₃ (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) and the reaction was stirred at that temperature for 1 h and quenched by pouring onto water or ice-water. The resulting mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH₄OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt: 1H NMR (500 MHz, MeOD) δ 7.57 (dd, J=7.9, 1.8 Hz, 1H), 7.48 (dd, J=7.8, 1.8 Hz, 1H), 7.35 (dd, J=7.9, 1.7 Hz, 1H), 7.29 (dd, J=7.8, 1.6 Hz, 1H), 7.10 (d, J=0.7 Hz, 1H), 5.75 (s, 1H), 3.28-3.19 (m, 3H), 2.55 (s, 3H), 1.50 (d, J=6.4 Hz, 3H). ESI MS m/z 399 [C₂₁H₁₉ClN₂O₂S+H]⁺.

Example 616 9-Bromo-2-fluoro-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one

To a stirred solution of diidopropylamine (84 μL 0.6 mmol) in THF (2.5 mL) at −78° C. was added n-BuLi (2.5M, 0.24 mL, 0.6 mmol). The resulting mixture was stirred at 0° C. for 10 min and then cooled at −78° C. A solution of 9-bromo-8-methoxy-6-methyl-5-((2-(trimethylsilyl ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.23 g, 0.50 mmol) in THF (1 mL) was added dropwise and the resulting mixture was stirred at −78° C. for 30 min. A solution of N-fluorobenzenesulfonimide (0.32, 1.0 mmol) in THF (1 mL) was added and the mixture was stirred at −78° C. for 2 h. The reaction was quenched by adding saturated ammonium chloride and extracted with dichloromethane (2×). The combined extracts were dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was purified by column chromatography (heptane/ethyl acetate) to afford the desired product (98 mg, 41%) as a white solid: ESI MS m/z 472 [C₁₉H₂₃BrFNO₃SSi+H]⁺.

Example 617 (R)-tert-butyl 2-(4-(2-fluoro)-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Following General Procedure B, (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (0.11 g, 0.31 mmol) was reacted with 9-bromo-2-fluoro-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (98 mg, 0.21 mmol) to afford the desired product (0.11 g, 85%) as a solid: ESI MS m/z 627 [C₃₃H₄₃FN₂O₂SSi+H]⁺.

Example 1375 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-2-fluoro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

To a solution (R)-tert-butyl 2-(4-(2-fluoro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (17 mg, 0.027 mmol) in CH₂C2 (1 mL) at rt was added trifluoroacetic acid (1.0 mL) and the reaction was stirred at that temperature for 2 h. The mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH₄OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product (5 mg, 43%) as a hydrochloride salt: ¹H NMR (500 MHz, CD₃OD) δ 7.52 (dd, J=7.8, 1.5 Hz, 1H), 7.47 (dd, J=7.7, 1.5 Hz, 1H), 7.32 (s, 1H), 7.31-7.22 (m, 2H), 5.30 (d, J=2.7 Hz, 1H), 3.29-3.18 (m, 3H), 2.63 (s, 3H), 1.47 (d, J=6.1 Hz, 3H): ESI MS m/z 397 [C₂₂H₂₁FN₂O₂S+H]⁺.

Example 1383 (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-2-fluoro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one

To a solution of (R)-tert-butyl 2-(4-(2-fluoro-8-methoxy-6-methyl-4-oxo-5-((2-(trimethylsilyl)ethoxy)methyl)-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (60 mg, 0.096 mmol) in CH₂Cl₂ (1 mL) at 0° C. was added BBr₃ (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) and the reaction was stirred at that temperature for 1 h and quenched by pouring onto water or ice-water. The resulting mixture was concentrated and the residue was dissolved methanol (2 mL) and treated with NH₄OH (2 mL). The resulting mixture was stirred at rt for 2 h and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired fractions were combined, concentrated and the residue was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a hydrochloride salt: ¹H NMR (500 MHz, CD₃OD) δ 7.55 (dd, J=7.9, 1.7 Hz, 1H), 7.46 (dd, J=7.8, 1.8 Hz, 1H), 7.32 (dd, J=23.9, 7.9 Hz, 2H), 7.10 (s, 1H), 5.46 (d, J=2.9 Hz, 1H), 3.28-3.15 (m, 3H), 2.55 (s, 3H), 1.49 (d, J=6.3 Hz, 3H); ESI MS m/z 383 [C₂₁H₁₉FN₂O₂S+H]⁺.

Example 618 tert-butyl 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

To a solution of tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (0.96 g, 2.1 mmol) in dichloromethane (15 mL) at 0° C. was added BBr₃ (1.0 M in methylene chloride, 15 mL, 15 mmol) and the reaction was stirred at that temperature for 1 h and quenched by pouring onto water or ice-water. The precipitate was filtered and suspended in DMF (8 mL). Di-tert-butyl dicarbonate (0.85 g, 3.9 mmol) and triethylamine (1.1 mL, 7.8 mmol) were added and the mixture was stirred at rt for 2 h. Water was added and the precipitate was filtered and purified by column chromatography to afford the desired product as a solid: ESI MS m/z 437 [C₂₄H₂₄N₂O₄S+H]⁺.

Example 619 tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate

To a solution of tert-butyl 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (44 mg, 0.10 mmol) in THF (2 mL) at 0° C. was added NaH (60%, 6 mg, 0.15 mmol) and the reaction was stirred at that temperature for 1 h. Isopropyl chloroformate (21 μL, 0.15 mmol) was added and the resulting mixture was stirred at rt for 3 h. Water was added and the mixture was extracted with dichloromethane (2×15 mL). The combined extracts were dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was purified by column chromatography (heptane/ethyl acetate) to afford the desired product (26 mg, 50%) as a solid: ESI MS m/z 523 [C₂₈H₃₀N₂O₆S+H]⁺.

Example 1077 9-(4-(1-Aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl isopropyl carbonate Hydrochloride

Following General Procedure C, tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (20 mg, 0.038 mmol) was reacted with trifluoroacetic acid (3 mL) to afford the desired product (18 mg, quant.) as a light yellow solid: ESI MS m/z 423 [C₂₃H₂₂N₂O₄S+H]⁺.

Example 620

9-(4-(1-(tert-Butoxycarbonylamino)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl acetate

Following Procedure Preparing tert-butyl 1-(4-(8-(isopropoxycarbonyloxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate, (44 mg, 0.10 mmol) was reacted with acetic anhydride (11 μL, 0.12 mmol) to afford the desired product (30 mg, 63%) as a solid: ESI MS m/z 479 [C₂₆H₂₆N₂O₅S+H]⁺.

Example 1099 9-(4-(1-Aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl acetate Hydrochloride

Example 621 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide

Following General Procedure E, 2-(4-bromophenyl)propane-1-sulfonamide (0.12 g, 0.43 mmol) was reacted with 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one (0.14 g, 0.44 mmol) to afford the desired product (16 mg, 8%) as a brown solid: ESI MS m/z 443 [C₂₂H₂₂N₂O₄S₂+H]⁺.

Example 1419 2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide

Following General Procedure F, 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide (16 mg, 0.036 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (7.0 mg, 44%) as a light brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.68 (d, J=8.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.41 (d, J=8.4 Hz, 2H), 7.07 (s, 1H), 6.08 (d, J=5.4 Hz, 1H), 2.57 (s, 3H), 1.86 (s, 6H); ESI MS m/z 429 [C₂₁H₂₀N₂O₄S₂+H]⁺; HPLC 98.7%, t_(R)=8.51 min.

Example 1057 N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

Following General Procedure B, N-(1-hydroxypropan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (570 mg, 1.7 mmol) was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one, (471 mg, 1.5 mmol) to afford the desired product (109 mg, 16%) as an off-white powder. ESI MS m/z 445 [C₂₁H₂₀N₂O₅S₂+H]⁺;

Example 1062 N-(1-bromopropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

Following General Procedure F, N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (55 mg, 0.12 mmol) was reacted with tribromoborane (0.2 mL) to afford the desired product (48 mg, 79%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD); ESI MS m/z 494 [C₂₀H₁₇BrN₂O₄S₂+H]⁺; HPLC 99.0% (AUC), t_(R)=11.39 min;

Example 1090 N-(2-Hydroxyethyl)-4-(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl benzenesulfonamide

Following General Procedure B, N-(2-hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (268 mg, 0.82 mmol) was reacted with 9-bromo-8-methoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4(5H)-one, (268 mg, 0.68 mmol) to afford the desired product (68 mg, 16%) as an off-white solid: ¹H NMR: (300 MHz, DMSO-d6) ESI MS m/z 415 [C₂₁H₂₂O₃S+H]⁺; HPLC >99% (AUC), t_(R)=11.73 min;

Example 1094 N-(2-Bromoethyl)-4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide

Following General Procedure F, N-(2-hydroxyethyl-4-(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide (55 mg, 0.13 mmol) was reacted with tribromoborane (0.2 mL) to afford the desired product (11 mg, 18%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) ESI MS m/z 464 [C₂₀H₁₉BrN₂O₄S+H]⁺; HPLC 94.9% (AUC), t_(R)=14.88 min;

Example 622 2-(4-(8-Methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)phenylsulfonamido)ethyl methanesulfonate

To a stirred solution of N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide (230 mg, 0.555 mmol) and triethylamine (168 mg, 1.66 mmol) in anhydrous tetrahydrofuran (10 mL) was added methane sulfonyl chloride (88 mg, 0.666 mmol). The reaction mixture was stirred for 20 h at room temperature. After this time the reaction mixture was filtered to remove a white precipitate, which was washed with tetrahydrofuran (30 mL). The filtrate was concentrated under reduced pressure to an orange solid. The residue was purified by flash chromatography to afford the desired product as a brown solid (141 mg, 51%). ESI MS m/z 493 [C₂₂H₂₄N₂O₇S₂+H]⁺

Example 1145 N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-2,3,45-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)benzenesulfonamide

To a stirred solution of 2-(4-(8-methoxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-9-yl)phenylsulfonamido)ethyl methanesulfonate (141 mg, 0.286 mmol) in anhydrous dichloroethane (10 mL) was added aluminum chloride (190 mg, 1.43 mmol). The reaction mixture was stirred at reflux for 20 h. After this time the reaction was cooled to room temperature and concentrated under reduced pressure. The residue was treated with methanol (10 mL) and allowed to stand at room temperature for 1 h. Upon standing a precipitate formed and was subsequently filtered from the mother liquor. The precipitate was purified by preparatory HPLC (C18 silica, acetonitrile/water with 0.05% TFA gradient) to obtain the desired product (9 mg, 7.5%) as an off-white solid: ¹H NMR (500 MHz, DMSO-d) ESI MS m/z 419 [C₂₀H₁₉N₂O₄S+H]⁺; HPLC 97.6% (AUC), t_(R)=15.94 min.

Example 1154 (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 1-(4-(6-chloro-%-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (100 mg, 0.194 mmol was reacted with tribromoborane (1.0 M in methylene chloride 1.16 mL, 1.16 mmol) to afford the desired product (35 mg, 45%) as a white solid: ¹H NMR (500 MHz, DMSO) δ 10.81 (d, J=10.5 Hz, 1H), 9.83 (s, 1H), 9.70-9.45 (m, 1H), 9.28 (s, 1H), 7.73 (d, J=5.4 Hz, 1H), 7.70-7.60 (m, 2H), 7.38 (dd, J=12.4, 4.7 Hz, 3H), 5.70 (d, J=5.4 Hz, 1H), 4.19 (dt, J=12.1, 6.0 Hz, 1H), 2.51 (s, 3H), 2.20 (ddd, J=14.4, 9.5, 5.9 Hz, 1H), 2.02-1.89 (m, 1H), 0.84 (t, J=7.4 Hz, 31); ESI MS m/z 399 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC 96.9% (AUC), t_(R)=9.36 min.

Example 1148 (S)-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (135 mg, 0.282 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.69 mL, 1.69 mmol) to afford the desired product (48 mg, 47%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.62 (ddd, J=11.7, 8.0, 1.7 Hz, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.51-7.40 (m, 3H), 7.19 (d, J=8.9 Hz, 1H), 5.97 (d, J=5.4 Hz, 1H), 4.22 (dd, J=10.7, 4.6 Hz, 1H), 2.70 (s, 3H), 2.34-2.02 (m, 2H), 1.04-0.96 (m, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 95.9% (AUC), t_(R)=8.38 min.

Example 1181 (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.20 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.2 mL, 1.2 mmol) to afford the desired product (35 mg, 46%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.62 (d, J=5.4 Hz, 1H), 7.56 (dd, J=7.9, 1.9 Hz, 1H), 7.48 (dd, J=7.8, 1.9 Hz, 1H), 7.36 (dd, J=7.9, 1.7 Hz, 1H), 7.34-7.29 (m, 2H), 6.12 (d, J=5.4 Hz, 1H), 3.29-3.15 (m, 3H), 1.49 (d, J=6.5 Hz, 3H); ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.74 min.

Example 1163 (S)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (110 mg, 0.236 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.42 mL, 1.42 mmol) to afford the desired product (38 mg, 47%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.61-7.53 (m, 2H), 7.47 (dd, J=7.8, 1.9 Hz, 1H), 7.41 (dd, J=10.9, 6.1 Hz, 1H), 7.37 (dd, J=7.9, 1.7 Hz, 1H), 7.32 (dd, J=7.7, 1.7 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.15 (d, J=5.4 Hz, 1H), 3.29-3.17 (m, 3H), 1.50 (d, J=6.4 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.58 min.

Example 1116 9-(4-(1-(Aminomethyl)cyclopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl (1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (50 mg, 0.09 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.58 mL, 0.58 mmol) to afford the desired product (19 mg, 48%) as a white solid: ¹H NMR; (500 MHz, MeOD) δ 7.66-7.58 (m, 3H), 7.38-7.27 (m, 3H), 6.14 (d, J=5.4 Hz, 1H), 3.26 (s, 2H), 1.19 (t, J=5.5 Hz, 2H), 1.11 (t, J=5.5 Hz, 2H); ESI MS m/z 397 [C₂₁H₁₇ClN₂O₂S+H]⁺; HPLC 98.4% (AUC), t_(R)=9.24 min.

Example 1401 9-(4-(1-(Aminomethyl)cyclopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (100 mg, 0.22 mmol was reacted with tribromoborane (1.0 M in methylene chloride, 1.32 mL, 1.32 mmol) to afford the desired product (52 mg, 54%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.63 (t, J=6.8 Hz, 3H), 7.48 (s, 1H), 7.33 (d, J=8.2 Hz, 2H), 6.14 (d, J=5.4 Hz, 1H), 3.26 (s, 2H), 1.19 (t, J=5.6 Hz, 2H), 1.12 (t, J=5.5 Hz, 2H); ESI MS m/z 442 [C₂₁H₁₇BrN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.25 min.

Example 1254 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl(1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (120 mg, 0.24 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.46 mL, 1.46 mmol) to afford the desired product (38 mg, 42%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.60 (ddd, J=12.3, 7.1, 3.6 Hz, 3H), 7.34-7.29 (m, 2H), 7.08 (d, J=0.6 Hz, 1H), 6.19 (d, J=5.4 Hz, 1H), 3.25 (s, 2H), 2.57 (s, 3H), 1.22-1.06 (m, 4H); ESI MS m/z 377 [C₂₃H₂₂N₂O₂S+H]⁺; HPLC 98.6% (AUC), t_(R)=8.97 min.

Example 1215 (S)-8-Hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl carbamate (50 mg, 0.10 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.61 mL, 0.61 mmol) to afford the desired product (12 mg, 32%) as a light yellow solid: ¹H NMR (500 MHz, MeOD) δ 7.60-7.53 (m, 2H), 7.47 (dd, J=7.8, 1.8 Hz, 1H), 7.35 (dd, J=7.9, 1.7 Hz, 1H), 7.30 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (s, 1H), 6.15 (d, J=5.4 Hz, 1H), 3.40-3.27 (m, 3H), 2.74 (s, 3H), 2.57 (s, 3H), 1.50 (d, J=6.6 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.88 min.

Example 1232 (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.209 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.25 mL, 1.25 mmol) to afford the desired product (38 mg, 52%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.60-7.52 (m, 2H), 7.45 (dd, J=7.8, 1.9 Hz, 1H), 7.35 (dd, J=7.9, 1.7 Hz, 1H), 7.29 (dd, J=7.7, 1.7 Hz, 1H), 7.08 (s, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.29-3.17 (m, 3H), 2.57 (s, 3H), 1.50 (d, J=6.4 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 98.0% (AUC), t_(R)=8.63 min.

Example 1264 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-chloro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (120 mg, 0.24 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.45 mL, 1.45 mmol) to afford the desired product (52 mg, 57%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.64 (d, J=5.4 Hz, 1H), 7.54 (d, J=7.8 Hz, 1H), 7.37 (d, J=1.4 Hz, 1H), 7.23 (dd, J=7.7, 1.4 Hz, 1H), 7.08 (s, 1H), 6.19 (d, J=5.4 Hz, 1H), 3.42-3.14 (m, 4H), 2.56 (s, 3H); ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC 98.2% (AUC), t_(R)=8.55 min.

Example 1268 9-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-chloro-4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (80 mg, 0.154 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.92 mL, 0.92 mmol) to afford the desired product (37 mg, 59%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.68 (d, J=5.4 Hz, 1H), 7.56 (d, J=7.8 Hz, 1H), 7.42 (d, J=1.7 Hz, 1H), 7.30 (s, 1H), 7.27 (dd, J=7.8, 1.7 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 3.39-3.25 (m, 4H); ESI MS m/z 405 [C₁₉H₁₄Cl₂N₂O₂S+H]⁺; HPLC 98.1% (AUC), t_(R)=9.17 min.

Example 1262 (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (150 mg, 0.313 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.9 mL, 1.9 mmol) to afford the desired product (85 mg, 74%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.63 (ddd, J=7.0, 5.5, 2.2 Hz, 2H), 7.57 (d, J=5.4 Hz, 1H), 7.43 (ddd, J=7.4, 6.1, 2.1 Hz, 2H), 7.08 (s, 1H), 6.05 (d, J=5.4 Hz, 1H), 4.47 (q, J=6.9 Hz, 1H), 2.71 (s, 3H), 2.57 (s, 3H), 1.79 (d, J=6.9 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.40 min.

Example 1135 (R)-6-bromo-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (R)-tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (100 mg, 0.18 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.1 mL, 1.1 mmol) to afford the desired product (38 mg, 48%) as a white solid: ¹H NMR (500 MHz, DMSO) δ 10.20 (s, 1H), 9.88 (s, 1H), 9.76-9.59 (m, 1H), 9.37-9.21 (m, 1H), 7.78 (d, J=5.4 Hz, 1H), 7.74-7.64 (m, 2H), 7.54 (s, 1H), 7.40-7.33 (m, 2H), 5.77 (d, J=5.4 Hz, 1H), 4.44 (dd, J=12.5, 6.4 Hz, 1H), 2.50 (s, 3H), 1.68 (d, J=6.8 Hz, 3H); ESI MS m/z 429 [C₂₀H₁₇BrN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.00 min.

Example 1271 9-(4-(1-Amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (130 mg, 0.26 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.57 mL, 1.57 mmol) to afford the desired product (35 mg, 35%) as a white solid: ¹H NMR (500 MHz, DMSO) δ 11.81 (s, 1H), 9.34 (s, 1H), 7.98 (s, 3H), 7.72 (d, J=5.4 Hz, 1H), 7.49 (t, J=8.5 Hz, 1H), 7.40 (d, J=8.9 Hz, 1H), 7.17 (t, J=9.0 Hz, 1H), 7.12 (ddd, J=10.7, 9.7, 1.7 Hz, 2H), 6.02 (d, J=5.4 Hz, 1H), 3.25 (s, 2H), 1.51 (d, J=9.1 Hz, 6H); ESI MS m/z 383 [C₂₁H₁₉FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.77 min.

Example 1278 9-(4-(1-Amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (50 mg, 0.10 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.58 mL, 0.58 mmol) to afford the desired product (22 mg, 58%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.64 (d, J=5.4 Hz, 1H), 7.57 (t, J=8.4 Hz, 1H), 7.15 (ddd, J=15.1, 10.7, 1.7 Hz, 2H), 7.08 (d, J=0.7 Hz, 1H), 6.26 (d, J=5.4 Hz, 1H), 3.31 (s, 2H), 2.57 (s, 3H), 1.62 (d, J=5.6 Hz, 6H); ESI MS m/z 397 [C₂₂H₂₁FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.07 min.

Example 1291 9-(4-(1-Aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (100 mg, 0.23 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.4 mL, 1.4 mmol)) to afford the desired product (42 mg, 55%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.57-7.50 (m, 2H), 7.40 (ddd, J=18.8, 7.8, 1.8 Hz, 2H), 7.31 (dd, J=7.7, 1.7 Hz, 1H), 7.09 (d, J=0.8 Hz, 1H), 6.13 (d, J=5.4 Hz, 1H), 3.25 (ddd, J=26.6, 13.1, 7.1 Hz, 2H), 2.93 (dq, J, J=15.3, 5.2 Hz, 1H), 2.57 (d, J=0.6 Hz, 3H), 1.97-1.74 (m, 2H), 0.99 (t, J=7.4 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.21 min.

Example 1120 (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (100 mg, 0.22 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.3 mL, 1.3 mmol) to afford the desired product (28 mg, 38%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.65-7.58 (m, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.46-7.40 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.2, 5.9 Hz, 1H), 2.21-2.03 (m, 2H), 1.04 (t, J=7.4 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.24 min.

Example 1290 9-(4-(1-(Aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (130 mg, 0.32 mmol was reacted with tribromoborane (1.0 M in methylene chloride, 1.9 mL, 1.9 mmol to afford the desired product (82 mg, 65%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.63 (d, J=5.4 Hz, 1H), 7.46-7.41 (m, 2H), 7.38-7.32 (m, 2H), 7.09 (d, J=0.7 Hz, 1H), 6.26 (d, J=5.4 Hz, 1H), 3.36-3.33 (m, 2H), 2.65 (dd, J=21.2, 9.3 Hz, 2H), 2.58 (s, 3H), 2.45-2.37 (m, 2H), 2.27 (ddd, J=17.7, 11.5, 8.6 Hz, 1H), 2.12-2.01 (m, 1H); ESI MS m/z 391 [C₂₃H₂₂N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.37 min.

Example 1300 9-(4-(1-(Aminomethyl)cyclobutyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (100 mg, 0.20 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.23 mL, 1.23 mmol) to afford the desired product (52 mg, 68%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.64 (d, J=5.4 Hz, 1H), 7.44 (ddd, J=17.8, 10.5, 3.8 Hz, 3H), 7.39-7.35 (m, 2H), 7.19 (d, J=8.9 Hz, 1H), 6.25 (d, J=5.4 Hz, 1H), 3.44 (s, 2H), 2.65 (dd, J=21.3, 9.4 Hz, 2H), 2.46-2.36 (m, 2H), 2.33-2.20 (m, 1H), 2.14-2.00 (m, 1H); ESI MS m/z 377 [C₂₂H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.00 min.

Example 1309 9-(4-(1-Aminobutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5 dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (100 mg, 0.21 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.25 mL, 1.25 mmol) to afford the desired product (45 mg, 60%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.58-7.50 (m, 2H), 7.46-7.36 (m, 3H), 7.32 (dt, J=12.4, 6.2 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 6.11 (d, J=5.4 Hz, 1H), 3.40-3.19 (m, 2H), 2.95 (dq, J=15.3, 5.2 Hz, 1H), 1.98-1.85 (m, 1H), 1.86-1.71 (m, 1H), 1.06-0.91 (m, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.15 min.

Example 1312 9-(4-(1-Aminobutan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (65 mg, 0.13 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.76 mL, 0.76 mmol) to afford the desired product (28 mg, 56%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.60 (d, J=5.4 Hz, 1H), 7.54 (dd, J=7.9, 1.8 Hz, 1H), 7.44 (dd, J=7.7, 1.8 Hz, 1H), 7.39 (dd, J=7.9, 1.8 Hz, 1H), 7.35-7.30 (m, 2H), 6.08 (d, J=5.4 Hz, 1H), 3.38-3.22 (m, 2H), 2.98-2.89 (m, 1H), 1.97-1.85 (m, 1H), 1.85-1.72 (m, 1H), 0.98 (t, J=7.4 Hz, 3H); ESI MS m/z 399 [C₂₁H₁₉ClN₂O₂S+H]⁺; HPLC >99%, (AUC), t_(R)=10.29 min.

Example 385 9-(4-(1-(Ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl ethyl(1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)carbamate (150 mg, 0.31 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.9 mL, 1.9 mmol) to afford the desired product (37 mg, 33%) as a white glass: ¹H NMR (500 MHz, MeOD); δ 7.65 (dd, J=13.2, 4.9 Hz, 2H), 7.57 (d, J=5.4 Hz, 1H), 7.48-7.39 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.53 (q, J=6.8 Hz, 1H), 3.20-3.08 (m, 1H), 3.08-2.96 (m, 1H), 1.79 (d, J=6.9 Hz, 3H), 1.36 (t, J=7.3 Hz, 3H). ESI MS m/z 365 [+H]⁺; HPLC >99% (AUC), t_(R)=12.05 min.

Example 1165 6-chloro-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate (60 mg, 0.12 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.72 mL, 0.72 mmol) to afford the desired product (22 mg, 50%) as a white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 10.77 (s, 1H), 9.72 (s, 1H), 8.72 (s, 1H), 7.76 (d, J=5.4 Hz, 1H), 7.42 (d, J=8.1 Hz, 2H), 7.31 (s, 1H), 7.24 (d, J=8.1 Hz, 2H), 5.85 (d, J=5.4 Hz, 1H), 3.30-3.23 (m, 2H), 3.09-3.02 (m, 2H), 2.65 (s, 3H); ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.03 min.

Example 1197 (S)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (100 mg, 0.21 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.25 mL, 1.25 mmol) to afford the desired product (31 mg, 41%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.61-7.53 (m, 2H), 7.48 (dd, J=7.8, 1.9 Hz, 1H), 7.44-7.37 (m, 2H), 7.33 (dd, J=7.7, 1.7 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.14 (d, J=5.4 Hz, 1H), 3.41-3.25 (m, 3H), 2.75 (s, 3H), 1.50 (d, J=6.8 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.36 min.

Example 1224 9-(4-(2-aminoethyl)-2-bromo-5-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (tert-butyl 5-bromo-2-hydroxy-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (50 mg, 0.90 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.54 mL, 0.54 mmol) to afford the desired product (18 mg, 48%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.68 (d, J=5.5 Hz, 1H), 7.58 (s, 1H), 7.44 (d, J=9.0 Hz, 1H), 7.18 (d, J=9.0 Hz, 1H), 6.82 (s, 1H), 6.33 (d, J=5.5 Hz, 1H), 3.25 (m, 2H), 2.95 (m, 2H); ESI MS m/z 432 [C₁₉H₁₅BrN₂O₃S+H]⁺; HPLC 96.9% (AUC), t_(R)=8.10 min.

Example 1082 (S)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (100 mg, 0.22 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.30 mL, 13.0 mmol) to afford the desired product (50 mg, 66%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.68-7.61 (m, 2H), 7.57 (d, J=5.4 Hz, 1H), 7.49-7.39 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.04 (d, J=5.4 Hz, 1H), 4.48 (q, J=6.8 Hz, 1H), 2.72 (s, 3H), 1.80 (d, J=6.9 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC 96.9% (AUC), t_(R)=7.68 min.

Example 1088 9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (40 mg, 0.08 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.48 mL, 0.48 mmol) to afford the desired product (12 mg, 40%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.65-7.56 (m, 3H), 7.46-7.39 (m, 2H), 7.30 (s, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.1, 6.0 Hz, 1H), 2.21-2.02 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 385 [C₂₀H₁₇N₂O₂S+H]⁺; HPLC 95.9% (AUC), t_(R)=9.15 min.

Example 1087 (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (40 mg, 0.08 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.48 mL, 0.48 mmol) to afford the desired product (18 mg, 60%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.72-7.60 (m, 3H), 7.49-7.39 (m, 2H), 7.30 (s, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.49 (q, J=6.9 Hz, 1H), 2.73 (d, J=4.3 Hz, 3H), 1.80 (d, J=6.9 Hz, 3H); ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=13.60 min.

Example 1209 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-ethyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (200 mg, 0.40 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 2.37 mL, 2.37 mmol) to afford the desired product (120 mg, 78%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.62 (d, J=8.4 Hz, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.41 (dd, J=15.2, 8.6 Hz, 3H), 7.19 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 3.34 (s, 2H), 2.05-1.88 (m, 4H), 0.93 (t, J=7.4 Hz, 6H); ESI MS m/z 393 [C₂₁H₂₄N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.38 min.

Example 1271 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (80 mg, 0.16 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (35 mg, 56%) as a yellow glass: ¹H NMR (500 MHz, MeOD) δ 7.67 (d, J=5.4 Hz, 1H), 7.59 (t, J=8.4 Hz, 1H), 7.44 (d, J=8.9 Hz, 1H), 7.20 (d, J=8.9 Hz, 3H), 6.25 (d, J=5.4 Hz, 1H), 3.54 (d, J=13.0 Hz, 2H), 3.28 (s, 1H), 1.63 (d, J=4.6 Hz, 6H); ESI MS m/z 383 [C₂₁H₁₉FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.89 min.

Example 623 tert-butyl (1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate

Following General Procedure I, tert-butyl (1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (750 mg, 1.57 mmol) was reacted with NBS (280 mg, 1.57 mmol)) to afford the desired product (473 mg, 54%) as a yellow solid: ESI MS m/z 555 [C₂₇H₂₇BrN₂O₄S+H]⁺.

Example 624 (S)-tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Following General Procedure I, (S)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (1.0 g, 2.0 mmol was reacted with NBS (446 mg, 2.5 mmol) to afford the desired product (500 mg, 43%) as a yellow solid: ESI MS m/z 557 [C₂₇H₂₉BrN₂O₄S+H]⁺.

Example 625 (R)-tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate

Following General Procedure I, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (400 mg, 0.86 mmol) was reacted with NBS (184 mg, 1.03 mmol) to afford the desired product (285 mg, 61%) as a yellow solid: ESI MS m/z 543 [C₂₆H₃₀BrN₂O₄S+H]⁺.

Example 1263 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, tert-butyl 2-chloro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (50 mg, 0.10 mmol) was reacted with TFA (3.0 mL) to afford the desired product as a light yellow solid (27 mg, 68%): ¹H NMR (500 MHz, MeOD) δ 7.62 (t, J=5.8 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.35 (d, J=1.6 Hz, 1H), 7.29 (s, 1H), 7.21 (dd, J=7.7, 1.7 Hz, 1H), 6.11 (d, J=5.4 Hz, 1H), 3.75 (d, J=7.4 Hz, 3H), 3.38-3.16 (m, 4H), 2.64 (s, 3H); ESI MS m/z 399 [C₂₁H₁₉ClN₂O₂S+H]⁺; HPLC 98.8% (AUC), t_(R)=9.50 min.

Example 1265 (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (50 mg, 0.10 mmol) was reacted with TFA (3.0 mL) to afford the desired product as a yellow solid 25 mg, 63%): ¹H NMR (500 MHz, MeOD) δ 7.64 (d, J=8.4 Hz, 2H), 7.57 (d, J=5.4 Hz, 1H), 7.38 (d, J=8.6 Hz, 2H), 7.29 (s, 1H), 5.99 (d, J=5.4 Hz, 1H), 4.48 (q, J=6.8 Hz, 1H), 3.73 (s, 3H), 2.72 (s, 3H), 2.64 (s, 3H), 1.80 (d, J=6.9 Hz, 3H). ESI MS m/z 379 [C₂₂H₂₁N₂O₂S+H]⁺; HPLC 98.0% (AUC), t_(R)=9.51 min.

Example 1277 9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butylcarbamate (40 mg, 0.08 mmol) was reacted with TFA (3.0 mL) to afford the desired product as a white solid 14 mg, 44%): ¹H NMR (500 MHz, MeOD) δ 7.54-7.47 (m, 2H), 7.42 (dd, J: 7.7, 1.8 Hz, 1H), 7.35-7.25 (m, 3H), 5.96 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.37-3.26 (m, 2H), 3.02-2.89 (m, 1H), 2.64 (s, 3H), 1.97-1.85 (m, 1H), 1.81-1.67 (m, 1H), 0.96 (t, J=7.3 Hz, 3H); ESI MS m/z 39.3 [C₂₃H₂₄N₂O₂S+H]⁺; HPLC >99% (AUC), L_(R)=9.74 min.

Example 1064 (S)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl(methyl)carbamate (30 mg, 0.06 mmol) was reacted with TFA (1.5 mL) to afford the desired product (15 mg, 65%) as a white solid: ¹H NMR (500 MHz, MeOD); δ 7.64 (d, J=8.5 Hz, 2H), 7.61-7.52 (m, 2H), 7.45-7.36 (m, 3H), 5.98 (d, J=5.4 Hz, 1H), 4.48 (q, J=6.8 Hz, 1H), 3.74 (s, 3H), 2.73 (s, 3H), 1.79 (t, J=8.0 Hz, 3H). ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=13.69 min.

Example 1121 (S)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, (S)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (40 mg, 0.09 mmol) was reacted with TFA (2.0 mL) to afford the desired product (15 mg, 49%) as a light yellow glass: ¹H NMR (500 MHz, MeOD)) δ 7.60 (tt, J=7.1, 3.6 Hz, 2H), 7.57-7.51 (m, 2H), 7.42-7.36 (m, 3H), 6.00 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.2, 6.0 Hz, 1H), 3.73 (s, 3H), 2.11 (qdd, J=13.6, 8.3, 6.7 Hz, 3H), 1.08-0.98 (m, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.74 min.

Example 1391 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, tert-butyl (1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (50 mg, 0.09 mmol) was reacted with TFA (5.0 mL) to afford the desired product (19 mg, 47%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.71-7.65 (m, 1H), 7.65-7.57 (m, 3H), 7.32-7.27 (m, 2H), 5.99 (t, J=6.4 Hz, 1H), 3.75 (s, 3H), 3.29 (s, 2H), 1.21-1.10 (m, 4H); ESI MS m/z 456 [C₂₂H₁₉BrN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=10.83 min.

Example 1251 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, tert-butyl (1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropyl)methylcarbamate (70 mg, 0.14 mmol) was reacted with TFA (4.0 mL) to afford the desired product (32 mg, 56%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.63-7.51 (m, 3H), 7.32-7.23 (m, 3H), 6.02 (d, J=5.4 Hz, 1H), 3.74 (s, 3H), 3.28 (s, 2H), 2.64 (s, 3H), 1.21-1.08 (m, 4H); ESI MS m/z 391 [C₂₃H₂₂N₂O₂S+H]⁺; HPLC 95.7% (AUC), t_(R)=9.15 min.

Example 1297 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, tert-butyl(1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (200 mg, 0.42 mmol) was reacted with TFA (5.0 mL) to afford the desired product (150 mg, 89%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.61 (d, J=5.4 Hz, 1H), 7.47-7.41 (m, 2H), 7.35-7.30 (m, 3H), 6.07 (d, J=5.4 Hz, 1H), 3.76 (s, 3H), 3.46 (s, 2H), 2.65 (s, 3H), 2.64-2.57 (m, 2H), 2.47-2.37 (m, 2H), 2.32-2.15 (m, 1H), 2.12-1.97 (m, 1H); ESI MS m/z 405 [C₂₄H₂₄N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=12.27 min.

Example 1321 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C, tert-butyl(1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclobutyl)methylcarbamate (25 mg, 0.05 mmol) was reacted with TFA (2.5 mL) to afford the desired product (16 mg, 80%) as a white solid: ¹H NMR (500 MHz, MeOD) δ 7.66 (s, 1H), 7.55 (s, 1H), 7.47 (s, 2H), 7.34 (s, 2H), 6.04 (s, 1H), 3.77 (s, 3H), 3.47 (s, 2H), 2.68-2.54 (m, 2H), 2.47-2.35 (m, 2H), 2.31-2.20 (m, 1H), 2.12-2.02 (m, 1H); ESI MS m/z 426 [C₂₃H₂₁ClN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.87 min.

Example 1154 (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (100 mg, 0.194 mmol was reacted with tribromoborane (1.0 M in methylene chloride 1.2 mL, 1.16 mmol) to afford the desired product (35 mg, 45%) as a white solid: ¹H NMR (500 MHz, DMSO) δ 10.81 (d, J=10.5 Hz, 1H), 9.83 (s, 1H), 9.70-9.45 (m, 1H), 9.28 (s, 1H), 7.73 (d, J=5.4 Hz, 1H), 7.70-7.60 (m, 2H), 7.38 (dd, J=12.4, 4.7 Hz, 3H), 5.70 (d, J=5.4 Hz, 1H), 4.19 (dt, J=12.1, 6.0 Hz, 1H), 2.51 (s, 3H), 2.20 (ddd, J=14.4, Z

Example 626 (S)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate

Following General Procedure J, (S)-tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (150 mg, 0.269 mmol) was reacted with trimethyl boroxine (102 mg, 0.8 mmol) to afford the desired product (95 mg, 75%) as a brown solid: ESI MS m/z 493 [C₂₈H₃₂BrN₂O₄S+H]⁺.

Example 1372 9-(4-(1-((dimethylamino)methyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride (110 mg, 0.28 mmol)) was reacted with formaldehyde (37% in water, 22 mg, 0.70 mmol) to afford the desired product as a white solid (28 mg, 25%): ¹H NMR (500 MHz, MeOD) δ 7.65 (t, J=7.4 Hz, 3H), 7.43 (d, J=8.1 Hz, 2H), 7.12 (s, 1H), 6.24 (d, J=5.3 Hz, 1H), 3.80 (s, 2H), 2.86 (s, 6H), 2.77-2.67 (m, 2H), 2.60 (s, 3H), 2.52 (dt, J=11.9, 8.8 Hz, 2H), 2.30-2.17 (m, 1H), 2.17-2.05 (m, 1H); ESI MS m/z 419 [C₂₅H₂₆N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.51 min.

Example 1172 (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (20 mg, 0.06 mmol)) was reacted with formaldehyde (37% in water, 5.0 mg, 0.15 mmol) to afford the desired product as a white solid (15 mg, 70%): ¹H NMR (500 MHz, MeOD) δ 7.64-7.51 (m, 3H), 7.45-7.37 (m, 2H), 7.34 (dd, J=7.7, 1.7 Hz, 1H), 7.19 (t, J=7.7 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.62 (td, J=11.5, 2.6 Hz, 1H), 3.50-3.40 (m, 2H), 2.97 (s, 3H), 2.94 (s, 3H), 1.48 (d, J=6.6 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.63 min.

Example 1128 (S)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (25 mg, 0.07 mmol)) was reacted with formaldehyde (37% in water, 5.5 mg, 0.18 mmol) to afford the desired product as a white solid (12 mg, 45%): ¹H NMR (500 MHz, MeOD) δ 7.66 (ddd, J=19.7, 7.7, 1.6 Hz, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.52-7.45 (m, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.20 (d, J=8.9 Hz, 1H), 5.95 (d, J=5.4 Hz, 1H), 4.38 (dd, J=11.3, 4.4 Hz, 1H), 2.99 (d, J=2.1 Hz, 3H), 2.85 (d, J=3.2 Hz, 3H), 2.40-2.18 (m, 2H), 1.03-0.93 (m, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC 98.4% (AUC), t_(R)=8.14 min.

Example 1127 (S)-9-(4-(1-(ethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (30 mg, 0.09 mmol)) was reacted with formaldehyde (37% in water, 9.5 mg, 0.21 mmol) to afford the desired product as a white solid (15 mg, 46%): ¹H NMR (500 MHz, MeOD) δ 7.68-7.57 (m, 2H), 7.54 (d, J=5.4 Hz, 1H), 7.45 (ddd, J=17.0, 10.1, 5.3 Hz, 3H), 7.19 (d, J=8.9 Hz, 1H), 5.97 (d. J=15.4 Hz, 1H), 4.26 (dd, J=11.1, 4.3 Hz, 1H), 3.11 (tt, J=14.6, 7.3 Hz, 1H), 3.05-2.95 (m, 1H), 2.25 (ddd, J=13.0, 7.4, 4.4 Hz, 1H), 2.09 (ddd, J=13.1, 11.2, 7.4 Hz, 1H), 1.35 (t, J=7.3 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC 98.4% (AUC), t_(R)=8.51 min.

Example 1095 9-(4-(2-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate (650 mg, 1.40 mmol) was reacted with BBr₃ (1.0 M in CH₂Cl₂, 10 mL, 10 mmol) to afford the desired product (152 mg, 31%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.56 (d, J=5.4 Hz, 1H), 7.49 (d, J=7.9 Hz, 1H), 7.43 (dd, J=13.3, 8.3 Hz, 2H), 7.34 (d, J=7.9 Hz, 2H), 7.18 (d, J=8.9 Hz, 1H), 6.11 (d, J=5.4 Hz, 1H), 3.71-3.60 (m, 1H), 3.05 (dd, J=7.2, 2.2 Hz, 2H), 1.40 (d, J=6.6 Hz, 3H): ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC 98.6% (AUC), t_(R)=8.08 min.

Example 1106 9-(4-(2-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, a tert-butyl 1-(4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propan-2-ylcarbamate (55 mg, 0.11 mmol) was reacted with BBr₃ (1.0 M in CH₂Cl₂, 2 mL, 2 mmol) to afford the desired product (28 mg, 66%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.61 (d, J=5.4 Hz, 1H), 7.47 (dd, J=22.8, 7.8 Hz, 2H), 7.36-7.29 (m, 3H), 6.08 (d, J=5.4 Hz, 1H), 3.65 (dd, J=13.7, 6.9 Hz, 1H), 3.05 (ddd, J=34.9, 13.6, 7.3 Hz, 2H), 1.39 (d, J=6.6 Hz, 3H): ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.77 min.

Example 379 9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 1387, 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (10 mg, 0.03 mmol) was reacted with paraformaldehyde (8 mg, 0.11 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (7.0 mg, 87%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.70 (d, J=7.9 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.39 (dd, J=25.8, 8.4 Hz, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 2.94 (s, 6H), 1.34-1.25 (m, 2H), 1.23-1.14 (m, 2H); ESI MS m/z 391 [C₂₃H₂₂N₂O₂S+H]⁺; HPLC 96.7% (AUC), t_(R)=8.72 min.

Example 373 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

To a solution of 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile (50 mg, 0.14 mmol) in toluene (13 mL) at 0° C. was added BH₃.THF (1.0 M, 13 mL, 13 mmol) and the reaction was warmed to room temperature and heated at reflux for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (5.4 mg, 10%): ¹H NMR (500 MHz, CD₃OD) δ 7.60-7.49 (m, 3H), 7.47 (dd, J=7.7, 1.7 Hz, 1H), 7.39 (d, J=9.1 Hz, 1H), 7.34-7.25 (m, 2H), 6.00 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.30-3.18 (m, 3H), 1.49 (d, J=6.5 Hz, 3H): ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 99% (AUC), t_(R)=8.76 min.

Example 1218 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-fluor-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate (70 mg, 0.14 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 5 mL, 5 mmol) to afford the desired product as a white solid (17 mg, 30%): ¹H NMR (500 MHz, CD₃OD) δ 7.66 (d, J=5.4 Hz, 1H), 7.54 (s, 1H), 7.50 (t, J=7.9 Hz, 1H), 7.10 (d, J=7.9 Hz, 2H), 6.09 (d, J=5.4 Hz, 1H), 3.76 (s, 3H), 3.25-3.06 (m, 4H); ESI MS m/z 403 [C₂₀H₁₆ClFN₂O₂S+H]⁺; HPLC 97.9% (AUC), t_(R)=9.63 min.

Example 1247 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (110 mg, 0.20 mmol) was treated with BBr₃ (1.0 M in CH₂Cl₂, 10 mL, 10 mmol) to afford the desired product as a brown solid (39 mg, 45%): ESI MS m/z 443 [C₂₁H₁₉BrN₂O₂S+H]⁺; HPLC 96.3% (AUC), t_(R)=9.56 min.

Example 1245 6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethyl(methyl)carbamate (90 mg, 0.16 mmol) in CH₂Cl₂ at 0° C. was added BBr₃ (1.0 M in CH₂Cl₂, 6 mL, 6 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a white solid (15 mg, 21%): ESI MS m/z 447 [C₂₀H₁₆BrFN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.26 min.

Example 1258 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate (60 mg, 0.12 mmol) in CH₂Cl₂ at 0° C. was added BBr₃ (1.0 M in CH₂Cl₂, 6 mL, 6 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a off-white solid (31 mg, 67%): ¹H NMR (500 MHz, (CD₃OD) 7.63 (d, J=5.4 Hz, 1H), 7.51 (t, J=7.9 Hz, 1H), 7.15-7.06 (m, 3H), 6.20 (d, J=5.4 Hz, 1H), 3.42-3.35 (m, 2H), 3.30-3.10 (m, 2H), 2.80 (s, 3H), 2.57 (s, 3H); ESI MS m/z 383 [C₂₁H₁₁FN₂O₂S+H]⁺, HPLC >99% (AUC), t_(R)=8.65 min.

Example 1260 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropylcarbamate (70 mg, 0.14 mmol) in CH₂C₂ at 0° C. was added BBr₃ (1.0 M in CH₂Cl₂, 5 mL, 5 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a brown solid (12 mg, 38%): ¹H NMR (500 MHz, CD₃OD) δ 7.66 (d, J=8.4 Hz, 2H), 7.63 (d, J=5.4 Hz, 1H), 7.36 (d, J=8.4 Hz, 2H), 7.32 (s, 1H), 6.13 (d, J=5.4 Hz, 1H), 3.29 (s, 2H), 1.58 (s, 6H); ESI MS m/z 399 [C₂₁H₁₉ClN₂O₂S+H]⁺; HPLC 98.8% (AUC), t_(R)=9.26 min.

Example 1280 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (120 mg, 0.24 mmol) in CH₂Cl₂ at 0° C. was added BBr₃ (1.0 M in CH₂Cl₂, 15 mL, 15 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a brown solid (40 mg, 43%): ¹H NMR (500 MHz, CD₃OD) δ 7.65 (ddd, J=9.9, 9.3, 6.1 Hz, 2H), 7.46-7.36 (m, 2H), 7.33-7.27 (m, 1H), 7.18 (t, J=9.0 Hz, 1H), 6.10 (dd, J=28.8, 5.4 Hz, 1H), 3.86-3.66 (m, 1H), 3.29-3.12 (m, 2H), 1.44-1.28 (m, 3H); ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.07 min.

Example 1111 9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (120 mg, 0.33 mmol) in CH₂Cl₂ at 0° C. was added BBr₃ (1.0 M in CH₂Cl₂, 5 mL, 5 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (48 mg, 42%): ¹H NMR (500 MHz, CD₃OD) δ 7.57 (dd, J=12.7, 6.7 Hz, 2H), 7.47 (d, J=6.9 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.37 (d, J=7.9 Hz, 1H), 7.32 (d, J=7.7 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.15 (d, J=5.4 Hz, 1H), 3.28-3.17 (m, 3H), 1.50 (d, J=6.1 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.25 min.

Example 1151 (R)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 1387, (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one hydrochloride (20 mg, 0.06 mmol) was reacted with paraformaldehyde (10 mg, 0.17 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (5 mg, 24%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.71 (dd, J=10.5, 7.8 Hz, 2H), 7.64 (d, J=5.4 Hz, 1H), 7.47 (t, J=7.1 Hz, 2H), 7.31 (d, J=8.9 Hz, 2H), 6.01 (d, J=5.4 Hz, 1H), 4.66 (q, J=6.9 Hz, 1H), 2.97 (s, 3H), 2.86 (s, 3H), 2.20-2.00 (m, 2H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 379 [C₁₂H₂₂N₂O₂S+H]⁺; HPLC 95.6% (AUC), t_(R)=8.92 min.

Example 1162 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butanenitrile

Following General Procedure F, 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl phenyl)butanenitrile (80 mg, 0.21 mmol) in CH₂Cl₂ at 0° C. was added BBr₃ (1.0 M in CH₂Cl₂, 3 mL, 3 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (4.3 mg, 6%): ¹H NMR (500 MHz, CD₃OD) δ 7.56 (dd, J=10.8, 4.6 Hz, 3H), 7.43-7.31 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.00 (d, J=5.4 Hz, 1H), 4.15 (t, J=7.2 Hz, 1H), 2.07 (p, J=7.3 Hz, 2H), 1.16 (t, J=7.4 Hz, 3H): ESI MS m/z 361 [C₂₁H₁₆N₂O₂S+H]⁺; HPLC 98.5% (AUC), t_(R)=12.2 min.

Example 1174 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (120 mg, 0.25 mmol) was reacted with TFA (10 mL) to afford the desired product (35 mg, 37%) as a off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.64 (dd, J=5.4, 3.1 Hz, 1H), 7.54 (ddd, J=25.0, 11.7, 5.2 Hz, 2H), 7.40 (dd, J=9.1, 1.1 Hz, 1H), 7.18-7.06 (m, 2H), 6.10 (dd, J=27.5, 5.4 Hz, 1H), 3.77 (s, 3H), 3.64-3.43 (m, 1H), 3.42-3.22 (m, 2H), 1.51 (d, J=7.0 Hz, 3H): ESI MS m/z 383 [C₂₁H₁₉FN₂O₂S+H]⁺; HPLC 96.5% (AUC), t_(R)=−9.07 min.

Example 1189 (R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure C (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (120 mg, 0.25 mmol) was reacted with TFA (8 mL) to afford the desired product (56 mg, 59%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.60-7.51 (m, 3H), 7.48 (dd, J=7.8, 1.9 Hz, 1H), 7.39 (d, J=9.1 Hz, 1H), 7.31 (ddd, J=15.8, 7.8, 1.8 Hz, 2H), 5.99 (d, J=5.4 Hz, 1H), 3.75 (s, 3H), 3.46-3.36 (m, 1H), 3.37-3.24 (m, 2H), 2.76 (s, 3H), 1.49 (d, J=6.7 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.96 min.

Example 1131 (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (R)-tert-butyl 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (70 mg, 0.15 mmol) in CH₂Cl₂ at 0° C. was added BBr₃ (1.0 M in CH₂Cl₂, 3 mL, 3 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (35 mg, 67%): ¹H NMR (500 MHz, CD₃OD) δ 7.61 (s, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.45-7.40 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.2, 5.9 Hz, 1H), 2.23-2.01 (m, 2H), 1.04 (t, J=7.4 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.06 min.

Example 1150 (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (R-tert-butyl 1-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (50 mg, 0.09 mmol) in CH₂Cl₂ at 0° C. was added BBr₃ (1.0 M in CH₂Cl₂, 5 mL, 5 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a light yellow solid (36 mg, 92%): ¹H NMR (500 MHz, CD₃OD) δ 7.65-7.57 (m, 3H), 7.50-7.46 (m, 1H), 7.45-7.39 (m, 2H), 6.02 (d, J=5.4 Hz, 1H), 4.32 (dd, J=9.2, 6.0 Hz, 1H), 2.20-2.00 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 429 [C₂₀H₁₇BrN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.17 min.

Example 254 N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl]methanesulfonamide

Following General Procedure F, N-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl]methanesulfonamide (47 mg, 0.11 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 3.0 mL, 3.0 mmol) to afford the desired product (17 mg, 39%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.58 (d, J=5.4 Hz, 1H), 7.55 (d, J=8.1 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 7.21 (s, 1H), 7.17-7.14 (m, 2H), 6.10 (d, J=5.4 Hz, 1H), 3.40 (s, 3H), 2.43 (s, 3H); ESI MS m/z 401 [C₁₉H₆N₂O₄S₂+H]⁺; HPLC 96.4% (AUC), t_(R)=10.23 min.

Example 334 9-[4-(2-Aminopropan-2-yl)phenyl]-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-[4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate (10 mg, 0.020 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (9.7 mg, 97%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.71 (d, J=8.4 Hz, 2H), 7.60 (d, J=5.4 Hz, 1H), 7.42 (d, J=8.4 Hz, 2H), 7.30 (s, 1H), 6.06 (d, J=5.4 Hz, 1H), 1.86 (s, 6H); ESI MS m/z 385 [C₂₀H₁₇ClN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=10.89 min

Example 329 9-[4-(Aminomethyl)phenyl]-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(6-chloro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (15 mg, 0.032 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1 mL, 1 mmol) to afford the desired product (10 mg, 80%) as a brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.64 (d, J=8.2 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.43-7.38 (m, 2H), 7.30 (s, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.27 (s, 2H); ESI MS m/z 357 [C₁₈H₁₃ClN₂O₂S+H]⁺; ESI MS m/z 357 [C₁₈H₁₃ClN₂O₂S+H]⁺; HPLC 98.4% (AUC), t_(R)=8.62 min.

Example 457 tert-Butyl 4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

Following the procedure from Example 463, 9-[4-(aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (320 mg, 1.0 mmol) was reacted with di-tert-butyl dicarbonate (260 mg, 1.2 mmol) to afford the desired product (150 mg, 36%): ESI MS m/z 323 [C₂₃H₂₂N₂O₄S+H]⁺.

Example 319 9-[4-(2-Aminopropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 2-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propan-2-ylcarbamate (29 mg, 0.063 mmol) was reacted with tribromoborane (1.0 M, 1.0 mL, 0.10 mmol) to afford the desired product (12 mg, 52%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.70 (d, J=8.4 Hz, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.46-7.37 (m, J=8.6, 7.7 Hz, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.07 (d, J=5.4 Hz, 1H), 1.86 (s, 6H); ESI MS m/z 351[C₂₀H₁₈N₂O₂S+H]⁺; HPLC 98.3% (AUC), t_(R)=10.48 min.

Example 270 9-[4-(Aminomethyl)phenyl]-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (10 mg, 0.019 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.0 mL, 1.0 mmol) to afford the desired product (3.9 mg, 47%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.64 (d, J=8.1 Hz, 2H), 7.60 (d, J=5.4 Hz, 1H), 7.47 (s, 1H), 7.42-7.40 (m, 2H), 6.08 (d, J=5.5 Hz, 1H), 4.27 (s, 2H); ESI MS m/z 403 [(C₁₈H₁₃BrN₂O₂S+2)+H]⁺; HPLC 97.1% (AUC), t_(R)=7.90 min.

Example 210 N-(2-Bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

Following General Procedure F, N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (1.7 g, 3.9 mmol) was reacted with tribromoborane (3.7 mL, 24 mmol) to afford the desired product (1.7 g, 91%) as an off-white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.84 (s, 1H), 9.43 (s, 1H), 8.16 (t, J=5.9 Hz, 1H), 7.94 (d, J=8.3 Hz, 2H), 7.75 (d, J=5.4 Hz, 1H), 7.52 (d, J=8.3 Hz, 2H), 7.41 (d, J=8.9 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 5.83 (d, J=5.4 Hz, 1H), 3.51 (t, J=6.4 Hz, 2H), 3.28 (q, J=6.2 Hz, 2H); ESI MS m/z 478 [C₁₉H₁₅BrN₂O₄S₂+H]⁺; HPLC 98.5% (AUC), t_(R)=15.23 min.

Example 458 2-{4-[8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl]phenylsulfonamido}ethyl methanesulfonate

To a solution of N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (390 mg, 0.90 mmol) and triethylamine (450 mg, 4.5 mmol) in anhydrous THF (20 mL) was added methane sulfonyl chloride (0.21 mL, 2.7 mmol) and the reaction mixture was stirred for 20 h at room temperature. The resulting precipitate was filtered and the filter cake was washed with THF (50 mL). The filtrate was concentrated and the residue was purified by flash chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product as a brown solid (250 mg, 55%). ¹H NMR (300 MHz, DMSO-d₆) δ 11.93 (s, 1H), 8.14 (t, J=11.7 Hz, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.79 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.53 (d, J=8.4 Hz, 2H), 7.43 (d, J=9.0 Hz, 1H), 5.74 (d, J=5.4 Hz, 1H), 4.24 (t, J=10.5 Hz, 2H), 3.71 (s, 3H), 3.20 (q, J=11.7 Hz, 2H) ESI MS m/z 509 [C₂₁H₂₀N₂O₇S₃+H]⁺

Example 332 N-(2-Chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

To a solution of 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylsulfonamido)ethyl methanesulfonate (250 mg, 0.49 mmol) in anhydrous dichloroethane was added aluminum chloride (330 mg, 2.5 mmol) and the reaction mixture was heated at reflux for 20 h. The reaction was cooled to room temperature, concentrated and quenched with methanol (10 mL). The resulting mixture was allowed to stand at room temperature for 1 h and the resulting precipitate was filtered and dried to afford the desired product (88 mg, 41%) as an off-white solid: ¹H NMR (500 MHz, DMSO-d) δ 11.83 (s, 1H), 9.42 (s, 1H), 8.13 (t, J=7.2 Hz, 1H), 7.94 (d, J=5.1 Hz, 2H), 7.74 (d, J=3.3 Hz, 1H), 7.51 (d, J=5.1 Hz, 2H), 7.41 (d, J=5.4 Hz, 1H), 7.18 (d, J=5.4 Hz, 1H), 5.82 (d, J=3.3 Hz, 1H), 3.65 (t, J=3.9 Hz, 2H), 3.22 (q, J=3.6 Hz, 2H); ESI MS m/z 435 [C₁₉H₁₅ClN₂O₄S₂+H]⁺; HPLC 97.2% (AUC), t_(R)=14.98 min,

Example 304 4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide

Following General Procedure F, the crude material from Example 74, 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide (33 mg, 0.080 mmol), was reacted with tribromoborane (0.2 mL) to afford the desired product (9 mg, 7% over 2 steps) as a brown solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.85 (s, 1H), 9.44 (s, 1H), 7.88 (dd, J=6.8, 1.6 Hz, 2H), 7.79 (d, J=5.4 Hz, 1H), 7.57 (dd, J=6.6, 1.7 Hz, 2H), 7.42 (d, J=8.9 Hz, 1H), 7.20 (d, J=8.9 Hz, 1H), 5.69 (d, J=5.4 Hz, 1H), 2.71 (s, 6H); ESI MS m/z 401 [C₁₉H₆N₂O₄S₂+H]⁺; HPLC 94.5% (AUC), t_(R)=14.84 min.

Example 297 N-(2-Bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

Following General Procedure F, 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (52 mg, 0.12 mmol) was reacted with tribromoborane (0.80 mL, 0.23 mmol) to afford the desired product (47 mg, 81%) as a white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.86 (s, 1H), 9.52 (s, 1H), 8.45 (t, J=5.7 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 7.80 (d, J=5.5 Hz, 1H), 7.46 (d, J=10.9 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.30 (dd, J=8.0, 1.4 Hz, 1H), 7.19 (d, J=9.0 Hz, 1H), 6.00 (d, J=5.4 Hz, 1H), 3.53 (t, J=6.3 Hz, 2H), 3.42 (q, J=6.0 Hz, 2H); ESI MS m/z 499 [C₁₉H₁₄BrFN₂O₄S₂+H]⁺; HPLC 98.3% (AUC), t_(R)=15.61 min.

Example 266 9-[5-(Aminomethyl)thiophen-2-yl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, tert-butyl [5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)thiophen-2-yl]methylcarbamate (30 mg, 0.067 mmol) was reacted with tribromoborane (0.50 mL) to afford the desired product (25 mg, 91%) as a off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.67 (d, J=5.4 Hz, 1H), 7.43 (d, J=9.0 Hz, 1H), 7.16-7.14 (m, 2H), 6.86 (d, J=3.5 Hz, 1H), 6.35 (d, J=5.4 Hz, 1H), 4.12 (s, 2H); ESI MS m/z 329 [C₁₆H₁₂N₂O₂S₂+H]⁺; HPLC 95.6% (AUC), t_(R)=9.59 min.

Example 235 9-{4-[(4-(Aminomethyl)piperidin-1-yl)methyl]-3-fluorophenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, tert-Butyl {1-[2-Fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]piperidin-4-yl}methylcarbamate (10 mg, 0.020 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.20 mL, 0.20 mmol) to afford the desired product (6.0 mg, 65%) as a light yellow solid: ¹H NMR (500 MHz, CD₃CN+D₂O) δ 7.73 (t, J=7.8 Hz, 1H), 7.63 (d, J=5.4 Hz, 1H), 7.46 (d, J=8.9 Hz, 1H), 7.24 (d, J=8.9 Hz, 1H), 7.21-7.18 (m, 2H), 6.07 (d, J=5.4 Hz, 1H), 4.45 (q, 14.0 Hz, 2H), 3.15-3.11 (m, 2H), 2.94-2.90 (m, 2H), 2.51 (s, 2H), 2.09-2.06 (m, 3H), 2.00-1.96 (m, 4H); ESI MS m/z 438 [C₂₄H₂₄FN₃O₂S+H]⁺; HPLC 94.6% (AUC), t_(R)=7.26 min.

Example 225 9-{4-[2-(Dimethylamino)ethyl]phenyl}-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 9-{4-[1-(dimethylamino)ethyl]phenyl}-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (6.0 mg, 0.015 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.10 mL, 0.075 mmol) to afford the desired product (5.2 mg, 90%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.72 (t, J=9.4 Hz, 2H), 7.63 (d, J=5.4 Hz, 1H), 7.46 (t, J=7.6 Hz, 2H), 7.04 (d, J=12.0 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.68 (q, J=4.3 Hz, 1H), 2.98 (s, 3H), 2.87 (s, 3H), 1.87 (d, J=7.0 Hz, 3H); ESI MS m/z 383 [C₂₁H₁₉FN₂O₂S+H]⁺; HPLC 96.0% (AUC), t_(R)=9.97 min.

Example 217 9-(4-Amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-(4-Amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (20 mg, 0.060 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.20 mL, 0.18 mmol) to afford the desired product (16 mg, 84%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.97 (d, J=1.7 Hz, 1H), 6.91 (dd, J=8.0, 1.7 Hz, 1H), 6.21 (d, J=5.4 Hz, 1H); ESI MS m/z 325 [C₁₇H₁₂N₂O₃S+H]⁺; HPLC 94.3% (AUC), t_(R)=8.17 min.

Example 93 9-{4-[2-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 9-{4-[2-(dimethylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (25 mg, 0.060 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.20 mL, 0.18 mmol) to afford the desired product (20 mg, 89%) as a yellow solid: ¹H NMR (500 MHz, CD₃CN+D₂O) δ 7.55 (d, J=5.4 Hz, 1H), 7.43-7.41 (m, 3H), 7.22-7.18 (m, 3H), 5.99 (d, J=5.4 Hz, 1H), 3.00 (s, 4H), 2.56 (s, 6H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 98.3% (AUC), t_(R)=9.24 min.

Example 341 9-{4-[1-(Dimethylamino)ethyl]phenyl}-6,7-difluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-{4-[1-(dimethylamino)ethyl]phenyl})-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one (20 mg, 0.050 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.50 mL, 0.50 mmol) to afford the desired product (15 mg, 72%) as an off-white solid: ¹H NMR (500 MHz, CD₃CN+D₂O) δ 7.68-7.67 (m, 2H), 7.61-7.59 (m, 1H), 7.43-7.41 (m, 2H), 5.86-5.84 (m, 1H), 4.58-4.54 (m, 1H), 2.86 (s, 3H), 2.76 (s, 3H), 1.79-1.77 (m, 3H); ESI MS m/z 401[C₂₁H₁₈F₂N₂O₂S+H]⁺; HPLC 97.8% (AUC), t_(R)=9.35 min.

Example 256 9-[4-(Aminomethyl)phenyl]-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl

4-(6-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (30 mg, 0.075 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.75 mL, 0.75 mmol) to afford the desired product (22 mg, 88%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.64 (d, J=8.0 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.39 (d, J=8.0 Hz, 2H), 7.02 (d, J=12.0 Hz, 1H), 6.07 (d, J=5.4 Hz, 1H), 4.28 (s, 2H); ESI MS m/z 341 [C₁₈H₁₃FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.34 min.

Example 335 (S)-9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, (S)-9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with formaldehyde (37% in water, 27 mg, 0.89 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (43 mg, 40%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.69 (q, J=7.8 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.48-7.42 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.65 (q, J=6.6 Hz, 1H), 2.97 (s, 3H), 2.87 (s, 3H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.30 min.

Example 459 (E)-9-[3-(3-Aminopiperidin-1-yl)prop-1-enyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, (E)-tert-Butyl 1-[3-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl]piperidin-3-ylcarbamate (320 mg, 0.88 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 4.0 mL, 4.0 mmol) to afford the desired product (100 mg, 41%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 8.00 (dd, J=19.3, 5.4 Hz, 2H), 7.32 (d, J=8.9 Hz, 1H), 7.24 (d, J=16.0 Hz, 1H), 7.12 (d, J=8.9 Hz, 1H), 6.39-6.25 (m, 1H), 4.25 (d, J=6.8 Hz, 1H), 3.94 (d, J=11.4 Hz, 1H), 3.83 (d, J=11.9 Hz, 1H), 3.76-3.65 (m, 1H), 3.28-3.10 (m, 2H), 2.24 (dd, J=35.1, 13.6 Hz, 2H), 2.06-1.98 (m, 1H), 1.81-1.68 (m, 1H).

Example 460 (E)-9-{3-[3-(Dimethylamino)piperidin-1-yl]prop-1-enyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

A solution of (E)-9-[3-(3-aminopiperidin-1-yl)prop-1-enyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (60 mg, 0.15 mmol) and formaldehyde (37% in water, 13 mg, 0.44 mmol) in methanol (1 mL) was stirred at room temperature for 30 min followed by the addition of sodium cyanoborohydride (28 mg, 0.44 mmol). The reaction mixture was stirred at room temperature overnight, concentrated and partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (30 mg, 53%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.97 (dd, J=19.4, 5.3 Hz, 2H), 7.30 (d, J=8.9 Hz, 1H), 7.23 (d, J=15.9 Hz, 1H), 7.07 (d, J=8.9 Hz, 1H), 6.33-6.22 (m, 1H), 4.32-4.18 (m, 3H), 3.90-3.77 (m, 2H), 3.47 (t, J=11.6 Hz, 1H), 3.18 (t, J=11.3 Hz, 1H), 3.01 (s, 6H), 2.40-2.23 (m, 2H), 2.10-1.84 (m, 2H).

Example 298 9-{3-[3-(Dimethylamino)piperidin-1-yl]propyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

To a solution of (E)-9-{3-[3-(dimethylamino)piperidin-1-yl]prop-1-enyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (20 mg, 0.052 mmol) in methanol (10 mL) under nitrogen was added Pd on carbon (10 wt %, 12 mg) and the reaction mixture was placed in a Parr shaker for 18 h under an atmosphere of hydrogen (40 psi). The reaction mixture was filtered over diatomaceous earth and the filtrate was concentrated. The residue was purified by preparatory HPLC (C18 Silica, water/acetonitrile w/0.05% TFA gradient) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (5.6 mg, 40%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 8.08 (d, J=5.4 Hz, 1H), 8.03 (d, J=5.4 Hz, 1H), 7.27 (d, J=8.8 Hz, 1H), 7.11 (d, J=8.8 Hz, 1H), 3.94-3.87 (m, 1H), 3.72-3.61 (m, 2H), 3.45-3.35 (m, 4H), 2.99-2.94 (m, 1H), 2.94 (s, 6H), 2.26-2.14 (m, 4H), 1.90-1.72 (m, 2H), 1.24 (s, 2H), 1.20 (s, 1H); ESI MS m/z 386 [C₂₁H₂₇N₃O₂S+H]⁺; HPLC >99% (AUC), t_(R)=6.71 min.

Example 267 9-{4-[(Ethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-{4-[(ethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (70 mg, 0.19 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.2 mL, 1.2 mmol) to afford the desired product (42 mg, 63%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.66 (d, J=8.2 Hz, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.43-7.41 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.34 (s, 2H), 3.22 (q, J=7.3 Hz, 2H), 1.41 (t, J=7.3 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.01 min.

Example 229 8-Hydroxy-9-{4-[(isopropylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-{4-[(isopropylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one was reacted with tribromoborane (1.0 M in methylene chloride, 1.6 mL, 1.6 mmol) to afford the desired product (48 mg, 50%) as a light brown glass: ¹H NMR (500 MHz, CD₃OD) δ 7.70 (d, J=7.6 Hz, 2H), 7.58 (d, J=9.7 Hz, 1H), 7.44-7.41 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.12 (d, J=5.1 Hz, 1H), 4.37 (s, 2H), 3.59-3.55 (m, 1H), 1.48 (d, J=6.5 Hz, 6H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >97.8% (AUC), t_(R)=7.93 min.

Example 212 N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl]methanesulfonamide

A solution of 9-[4-(aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (50 mg, 0.16 mmol) and methanesulfonyl chloride (43 mg, 0.37 mmol) in methylene chloride (5 mL) was stirred at room temperature for 10 min. N,N-diisopropylethylamine (48 mg, 0.37 mmol) was added and the reaction mixture was stirred for 1.5 h, concentrated under reduced pressure and the residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (28 mg, 45%) as a white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.77 (s, 1H), 9.22 (s, 1H), 7.70-7.67 (m, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.9 Hz, 1H), 7.23 (d, J=8.0 Hz, 2H), 7.15 (d, J=8.9 Hz, 1H), 5.89 (d, J=5.4 Hz, 1H), 4.29 (d, J=6.4 Hz, 2H), 2.94 (s, 3H); ESI MS m/z 401 [C₁₉H₁₆N₂O₄S+H]⁺; HPLC >99% (AUC), t_(R)=12.12 min.

Example 187 8-Hydroxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 8-methoxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.29 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.7 mL, 1.7 mmol) to afford the desired product (28 mg, 30%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.65 (d, J=8.1 Hz, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.44-7.41 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.05 (d, J=5.4 Hz, 1H), 4.33 (s, 2H), 2.83 (s, 3H); ESI MS m/z 337 [C₁₉H₁₆N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=10.02 min.

Example 184 9-{4-[(Diethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 9-{4-[(diethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.076 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.46 mL, 0.46 mmol) to afford the desired product (12 mg, 42%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.69 (d, J=8.1 Hz, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.48-7.42 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.50 (s, 2H), 3.36-3.31 (m, 4H), 1.43 (t, J=7.3 Hz, 6H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC 97.2% (AUC), t_(R)=8.27 min.

Example 165 9-{4-[(Dimethylamino)methyl]phenyl}hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 9-{4-[(dimethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.082 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.49 mL, 0.49 mmol) to afford the desired product (11 mg, 40%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.54-7.50 (m, 3H), 7.39 (d, J=8.9 Hz, 1H), 7.29 (d, J=8.0 Hz, 2H), 7.18 (d, J=8.9 Hz, 1H), 5.99 (d, J=5.5 Hz, 1H), 3.64 (s, 2H), 2.36 (s, 6H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC 98.5% (AUC), t_(R)=7.71 min.

Example 191 9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following the procedure outlined for Example 460, 9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (40 mg, 0.12 mmol) was reacted with formaldehyde (37% in water, 14 mg, 0.50 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (20 mg, 42%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.71-7.67 (m, 2H), 7.58 (d, J=4.4 Hz, 1H), 7.48-7.41 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.65 (q, J=7.0 Hz, 1H), 2.97 (s, 3H), 2.87 (s, 3H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=7.86 min.

Example 192 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-{4-[1-(dimethylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (3.2 g, 7.1 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 43 mL, 43 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (1.3 g, 92%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.71-7.67 (m, 2H), 7.58 (d, J=4.4 Hz, 1H), 7.48-7.41 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.65 (q, J=7.0 Hz, 1H), 2.97 (s, 3H), 2.87 (s, 3H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=7.86 min.

Example 72 9-[4-(Aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, tert-Butyl 4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (70 mg, 0.16 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.96 mL, 0.96 mmol) to afford the desired product (37 mg, 60%) as a white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.80 (s, 1H), 9.28 (s, 1H), 8.25 (br s, 2H), 7.68 (d, J=5.4 Hz, 1H), 7.60 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.9 Hz, 1H), 7.33 (d, J=8.1 Hz, 2H), 7.17 (d, J=8.8 Hz, 1H), 5.92 (d, J=5.4 Hz, 1H), 4.18 (m, 2H); ESI MS m/z 323 [C₁₈H₁₄N₂O₂S+H]⁺; HPLC 98.3% (AUC), t_(R)=10.74 min.

Example 73 9-[4-(Aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (260 mg, 0.60 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 3.6 mL, 3.6 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (120 mg, 50%) as a off-white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.80 (s, 1H), 9.28 (s, 1H), 8.25 (br s, 2H), 7.68 (d, J=5.4 Hz, 1H), 7.60 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.9 Hz, 1H), 7.33 (d, J=8.1 Hz, 2H), 7.17 (d, J=8.8 Hz, 1H), 5.92 (d, J=5.4 Hz, 1H), 4.18 (m, 2H); ESI MS m/z 323 [C₁₈H₁₄N₂O₂S+H]⁺; HPLC 98.3% (AUC), t_(R)=10.74 min.

Example 233 (S)-9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-9-[4-(1-aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.22 mmol) was reacted with tribromoborane (3.0 mL) to afford the desired product (16 mg, 22%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.63-7.61 (m, 2H), 7.56-7.55 (m, 1H), 7.43-7.41 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.61 (q, J=4.7 Hz, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 337 [C₁₉H₁₆N₂O₂S+H]⁺; HPLC 98.6% (AUC), t_(R)=7.62 min.

Example 347 (S)—N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethyl}methanesulfonamide

Following the procedure outlined for Example 301, (S)-9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with methanesulfonyl chloride (100 mg, 0.89 mmol) to afford the desired product (70 mg, 56%) as a light brown solid: ¹H NMR (500 MHz, CD₃OD) δ 5.89-7.55 (m, 2H), 7.52 (d, J=5.4 Hz, 1H), 7.38 (d J=8.9 Hz, 1H), 7.30-7.28 (m, 2H), 7.15 (d, J=8.9 Hz, 1H), 6.00 (d, J=5.4 Hz, 1H), 4.71 (q, J=7.1 Hz, 1H), 2.82 (s, 3H), 1.61 (d, J=7.0 Hz, 3H); ESI MS m/z 415 [C₂₀H₁₈N₂O₄S₂+H]⁺; HPLC >99% (AUC), t_(R)=12.43 min.

Example 339 9-{4-[1-(Dimethylamino)propyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, 9-[4-(1-aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.29 mmol) was reacted with formaldehyde (26 mg, 0.86 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (62 mg, 58%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.69-7.64 (m, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.51-7.47 (m, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 5.95 (d, J=5.4 Hz, 1H), 4.38 (dd, J=11.3, 4.3 Hz, 1H), 2.99 (s, 3H), 2.85 (s, 3H), 2.32-2.25 (m, 2H), 0.98 (t, J=7.3 Hz, 3H); ESI MS m/z 379 [C₂₂H₂₂N₂O₂S+H]⁺; HPLC 97.2% (AUC), t_(R)=9.45 min.

Example 338 9-{4-[1-(Diethylamino)propyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, (9-[4-(1-aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.29 mmol) was reacted with formaldehyde (38 mg, 0.86 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (52 mg, 45%) as a light brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.71 (dd, J=7.7, 1.8 Hz, 1H), 7.66 (dd, J=7.9 Hz, 1.9 Hz, 1H), 7.54 (d, J=5.5 Hz, 1H), 7.49-7.45 (m, 2H), 7.42 (d, J=5.5 Hz, 1H), 7.19 (d, J=4.2 Hz, 1H), 5.95 (d, J=5.4 Hz, 1H), 4.48 (dd, J=11.7, 3.8 Hz, 1H), 3.47-3.40 (m, 3H), 3.12-3.08 (m, 1H), 2.35-2.21 (m, 2H), 1.45 (t, J=7.3 Hz, 3H), 1.35 (t, J=7.3 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H); ESI MS m/z 407 [C₂₄H₂₆N₂O₂S+H]⁺; HPLC 96.3% (AUC), t_(R)=10.74 min.

Example 336 9-[4-(1-Aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl

1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propylcarbamate (70 mg, 0.15 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 0.90 mL, 0.90 mmol) to afford the desired product (35 mg, 52%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.63-7.58 (m, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.42-7.39 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.32 (q, J=5.9 Hz, 1H), 2.17-2.08 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=9.39 min.

Example 314 9-{4-[1-(Cyclopentylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-{4-[1-(cyclopentylamino)ethyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (200 mg, 0.48 mmol) was reacted with tribromoborane (15 mL) to afford the desired product (25 mg, 13%) as a brown solid: ¹H NMR (300 MHz, CD₃OD) δ 7.71-7.64 (m, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.48-7.41 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.06 (d, J=5.4 Hz, 1H), 4.57 (q, J=6.8 Hz, 1H), 3.59-3.49 (m, 1H), 2.26-2.08 (m, 2H), 1.87-1.62 (m, 9H); ESI MS m/z 405 [C₂₄H₂₄N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.84 min.

Example 313 8-Hydroxy-9-[4-(1-hydroxyethyl)phenyl]thieno[2,3-c]quinolin-4(5H)-one

A solution of 9-(4-acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (200 mg, 0.59 mmol) in ethanol (4 mL) was cooled to 0° C. and sodium borohydride (45 mg, 1.2 mmol) was added. The reaction mixture was stirred at room temperature for 18 h however starting material was present. The reaction was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 1.2 mL, 1.2 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction was cooled to 0° C., quenched with methanol and concentrated. The residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (2.6 mg, 1%) as a light brown solid: ¹H NMR (300 MHz, CD₃OD) δ 7.59-7.52 (m, 3H), 7.39 (d, J=8.9 Hz, 1H), 7.29-7.25 (m, 2H), 7.16 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.97 (q, J=6.4 Hz, 1H), 1.56 (d, J=6.5 Hz, 3H); ESI MS m/z 338 [C₁₉H₁₅NO₃S+H]⁺; HPLC 98.6% (AUC), t_(R)=9.78 min.

Example 308 9-{4-[1-(Dimethylamino)-2-methylpropan-2-yl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, 9-[4-(1-amino-2-methylpropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.082 mmol) was reacted with formaldehyde (7.4 mL, 0.25 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (7 mg, 22%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.71 (d, J=8.3 Hz, 2H), 7.56 (d, J=5.4 Hz, 1H), 7.40 (q, J=6.6 Hz, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.07 (d, J=5.4 Hz, 1H), 3.68 (s, 2H), 2.81 (s, 6H), 1.62 (s, 6H); ESI MS m/z 393 [C₂₃H₂₄N₂O₂S+H]⁺; HPLC 97.5% (AUC), t_(R)=8.46 min.

Example 301 (R)—N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethyl}methanesulfonamide

A solution of (R)-9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (28 mg, 0.83 mmol) and methanesulfonyl chloride (82 μL, 1.0 mmol) in 1:1 methylene chloride/THF (6 mL) and DMF (1.5 mL) was stirred at room temperature for 10 min followed by the addition of N,N-diisopropylethylamine (170 μL, 1.0 mmol). The reaction mixture was stirred for 1.5 h, concentrated and purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (8.9 mg, 2%) as a light brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.59-7.55 (m, 2H), 7.53 (d, J=5.5 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 7.31-7.30 (m, 2H), 7.16 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.71 (q, J=4.6 Hz, 1H), 2.82 (s, 3H), 1.62 (d, J=7.0 Hz, 3H); ESI MS m/z 415 [C₂₀H₁₈N₂O₄S₂+H]⁺; HPLC 96.4% (AUC), t_(R)=10.14 min.

Example 296 9-(4-Acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 9-(4-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (450 mg, 1.3 mmol) was reacted with tribromoborane (15 mL) to afford the desired product (320 mg, 74%) as a light brown solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.82 (s, 1H), 9.38 (s, 1H), 8.10 (d, J=8.3 Hz, 2H), 7.74 (d, J=5.4 Hz, 1H), 7.44-7.39 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 5.90 (d, J=5.4 Hz, 1H), 2.68 (s, 3H); ESI MS m/z 336 [C₁₉H₁₃NO₃S+H]⁺; HPLC 98.3% (AUC), t_(R)=10.59 min.

Example 290 3-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile

Following General Procedure F, 3-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]propanenitrile (45 mg, 0.13 mmol) was reacted with tribromoborane (3 mL) to afford the desired product (5.6 mg, 13%) as a white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.53 (d, J=5.4 Hz, 1H), 7.48 (d, J=7.9 Hz, 2H), 7.39 (d, J=8.9 Hz, 1H), 7.28 (d, J=7.9 Hz, 2H), 7.16 (d, J=8.9 Hz, 1H), 5.96 (d, J=5.4 Hz, 1H), 3.10 (t, J=3.8 Hz, 2H), 2.89 (t, J=7.1 Hz, 2H); ESI MS m/z 347 [C₂₀H₁₄N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=10.99 min.

Example 356 9-{4-[1-(Diethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

A solution of 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (40 mg, 0.11 mmol) and acetaldehyde (25 mg, 0.45 mmol) in methanol (2 mL) was stirred at room temperature for 30 min followed by the addition of sodium cyanoborohydride (28 mg, 0.452 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated, partitioned between water and ethyl acetate and the layers were separated. The aqueous layer was extracted with methylene chloride and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (30 mg, 65%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.84-7.82 (m, 1H), 7.67-7.65 (m, 1H), 7.44 (dd, J=9.1, 1.5 Hz, 1H), 7.34-7.28 (m, 2H), 7.19 (dd, J=8.9, 2.5 Hz, 1H), 6.14 (t, J=5.1 Hz, 1H), 5.16-5.06 (m, 1H), 3.46-3.35 (m, 3H), 3.30-3.15 (m, 1H), 2.79 (s, 1H), 1.88 (t, J=6.2 Hz, 3H), 1.48-1.37 (m, 6H); ESI MS m/z 411 [C₂₃H₂₃FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.57 min.

Example 359 9-[4-(1-Aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 1-[2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (400 mg, 0.856 mmol) was reacted with tribromoborane (4 mL) to afford the desired product (99 mg, 33%) as a white solid: ¹H NMR (300 MHz, CD₃OD) δ 7.70-7.60 (m, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.27-7.15 (m, 3H), 6.18 (q, J=3.0 Hz, 1H), 1.78 (t, J=6.5 Hz, 3H); ESI MS m/z 355 [C₁₉H₁₅FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=7.84 min.

Example 353 8-Hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 8-methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one (40 mL, 0.11 mmol) was reacted with tribromoborane (2 mL) to afford the desired product (26 mg, 68%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.56 (d, J=5.5 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.40 (d, J=8.9 Hz, 1H), 7.27-7.25 (m, 1H), 7.19 (br s, 1H), 7.16 (d, J=8.9 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 4.12 (s, 2H), 3.67-3.57 (m, 2H), 3.29-3.22 (m, 2H); ESI MS m/z 349 [C₂₀H₁₆N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=7.82 min.

Example 349 9-{4-[1-(Dimethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, 9-[4-(1-aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (40 mg, 0.11 mmol) was reacted with formaldehyde (14 mg, 0.45 mmol) to afford the desired product (23 mg, 53%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.81-7.73 (m, 1H), 7.66 (q, J=4.3 Hz, 1H), 7.44 (dd, J=8.9, 2.3 Hz, 1H), 7.34-7.29 (m, 2H), 7.20-7.18 (m, 1H), 6.14 (t, J=6.0 Hz, 1H), 5.03-4.92 (m, 1H), 3.03-2.86 (m, 6H), 2.78 (br s, 1H), 1.88 (dd, J=7.0, 2.4 Hz, 3H); ESI MS m/z 383 [C₂₁H₁₉FN₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.04 min.

Example 361 1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile

Following General Procedure F, 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile (340 mg, 0.91 mmol) was reacted with tribromoborane (1.3 mL) to afford the desired product (90 mg, 28%) as a light brown solid: ESI MS m/z 359 [C₂₁H₁₄N₂O₂S+H]⁺.

Example 348 9-{4-[1-(Aminomethyl)cyclopropyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 265, 1-[4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile (80 mg, 0.11 mmol) was reacted with borane (3 mL) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (20 mg, 28%) as a brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.62 (d, J=8.1 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.41 (d, J=8.9 Hz, 1H), 7.34 (d, J=8.0 Hz, 2H), 7.18 (d, J=8.9 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 3.25 (s, 2H), 1.21-1.12 (m, 4H); ESI MS m/z 363 [C₂₁H₁₈N₂O₂S+H]⁺; HPLC 97.3% (AUC), t_(R)=8.38 min.

Example 345 9-(2-Amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2,3-dihydro-1H-inden-2-ylcarbamate (210 mg, 0.59 mmol) was reacted tribromoborane (10 mL) to afford the desired product (55 mg, 27%) as a yellow solid:

Major Isomer: ¹H NMR (500 MHz, CD₃OD) δ 7.56 (d, J=2.4 Hz, 1H), 7.49 (d, J=7.7 Hz, 1H), 7.39 (d, J=1.3 Hz, 1H), 7.26 (s, 1H), 7.19-7.15 (m, 2H), 6.14 (d, J=5.4 Hz, 1H), 4.24-4.20 (m, 1H), 3.62-3.49 (m, 2H), 3.22-3.07 (m, 2H); ESI MS m/z 349 [C₂₀H₁₆N₂O₂S+H]⁺; HPLC 60.4% (AUC), t_(R)=7.89 min;

Minor Isomer: ¹H NMR (500 MHz, CD₃OD) δ 7.55 (d, J=2.4 Hz, 1H), 7.46 (d, J=7.7 Hz, 1H), 7.41 (d, J=1.3 Hz, 1H), 7.24 (s, 1H), 7.19-7.15 (m, 2H), 6.26 (d, J=5.4 Hz, 1H), 4.24-4.20 (m, 1H), 3.62-3.49 (m, 2H), 3.22-3.07 (m, 2H); ESI MS m/z 349 [C₂₀H₆N₂O₂S+H]⁺; HPLC 39.5% (AUC), t_(R)=7.65 min.

Example 327 9-{4-[2-(Dimethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-[4-(2-aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (25 mg, 0.063 mmol) was reacted with tribromoborane (3 mL) to afford the desired product (3.5 mg, 13%) as a brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.62 (d, J=5.4 Hz, 1H), 7.55 (t, J=7.9 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.18-7.11 (m, 3H), 6.15 (d, J=5.4 Hz, 1H), 3.52 (t, J=8.2 Hz, 2H), 3.26-3.19 (m, 1H), 3.04 (s, 6H); ESI MS m/z 383 [C₂₁H₁₉FN₂O₂S+H]⁺; HPLC 96.2% (AUC), t_(R)=8.06 min.

Example 278 9-{3-Fluoro-4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-{3-fluoro-4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one (90 mg, 0.21 mmol) was reacted with tribromoborane (2 mL) to afford the desired product (32 mg, 34%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.78-7.75 (m, 1H), 7.65 (d, J=5.3 Hz, 1H), 7.44 (d, J=8.9 Hz, 1H), 7.30-7.27 (m, 2H), 7.19 (d, J=8.9 Hz, 1H), 6.15-6.13 (m, 1H), 4.76-4.57 (m, 3H), 3.86-3.72 (m, 1H), 3.62-3.53 (m, 1H), 3.49-3.40 (m, 1H), 2.78 (br s, 1H), 2.54-2.46 (m, 1H), 2.22-2.20 (m, 1H), 2.15-2.05 (m, 1H); ESI MS m/z 411 [C₂₂H₁₉FN₂O₃S+H]⁺; HPLC >99% (AUC), t_(R)=7.58 min.

Example 277 9-[4-(1-Amino-2-methylpropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-[4-(1-amino-2-methylpropan-2-yl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.27 mmol) was reacted with tribromoborane (3 mL) to afford the desired product (25 mg, 22%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.66 (d, J=8.4 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.37 (d, J=8.3 Hz, 2H), 7.19 (d, J=8.9 Hz, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.28 (s, 2H), 1.59 (s, 6H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 96.9% (AUC), t_(R)=9.47 min.

Example 276 9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-[4-(2-aminoethyl)-3-fluorophenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (260 mg, 0.71 mmol) was reacted with tribromoborane (6 mL) to afford the desired product (12 mg, 12%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.52-7.49 (m, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.17 (d, J=8.9 Hz, 1H), 7.15-7.12 (m, 2H), 6.20 (d, J=5.4 Hz, 1H), 3.30-3.23 (m, 2H), 3.12-3.06 (m, 2H), 2.79 (br s, 3H); ESI MS m/z 355 [C₁₉H₁₅FN₂O₂S+H]⁺; HPLC 94.9% (AUC), t_(R)=7.80 min.

Example 275 (R)-9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (R)-tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (350 mg, 0.78 mmol) was reacted with tribromoborane (15 mL) to afford the desired product (120 mg, 42%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.65-7.62 (m, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.42-7.41 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.61 (q, J=4.5 Hz, 1H), 2.78 (br s, 3H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 337[C₁₉H₁₆N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=7.49 min.

Example 273 9-[4-(3-Aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-[4-(3-aminopropyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (140 mg, 0.39 mmol) was reacted with tribromoborane (6 mL) to afford the desired product (18 mg, 12%) as a light yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.53 (d, J=5.5 Hz, 1H), 7.43 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.9 Hz, 1H), 7.26 (d, J=8.1 Hz, 2H), 7.16 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.5 Hz, 1H), 3.04 (t, J=7.7 Hz, 2H), 2.88 (t, J=7.7 Hz, 2H), 2.11-2.08 (m, 2H); ESI MS m/z 351 [C₂₀H₁₈N₂O₂S+H]⁺; HPLC 96.2%, t_(R)=8.91 min.

Example 65 4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide

Following General Procedure F, N-tert-butyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (4.3 g, 9.9 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 48 mL, 48 mmol) to afford the desired product (3.4 g, 94%) as a light red solid: ¹H NMR (300 MHz, DMSO-d₆) δ 11.83 (s, 1H), 9.12 (s, 1H), 7.96-7.95 (m, 2H), 7.76 (d, J=5.4 Hz, 1H), 7.48-7.47 (m, 4H), 7.41 (d, J=8.9 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 5.91 (d, J=5.4 Hz, 1H); ESI MS m/z 373 [C₁₇H₁₂N₂O₄S₂+H]⁺; HPLC 98.1% (AUC), t_(R)=10.29 min.

Example 61 8-Hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 9-(1H-indazol-6-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (35 mg, 0.10 mmol) was reacted with tribromoborane (1.5 mL, 0.15 mmol) to afford the desired product (3.6 mg, 11%) as a light brown solid: ¹H NMR (500 MHz, CD₃OD) δ 8.17 (s, 1H), 7.75-7.73 (m, 2H), 7.48 (d, J=5.5 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.34 (d, J=9.2 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 5.91 (d, J=5.5 Hz, 1H); ESI MS m/z 334 [C₁₈H₁₁N₃O₂S+H]⁺; HPLC 96.3% (AUC), t_(R)=9.20 min.

Example 193 N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethyl}methanesulfonamide

A solution of 9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.089 mmol) and methanesulfonyl chloride (9.0 μL, 0.11 mmol) in 2:1 methylene chloride/THF (3 mL) was stirred at room temperature for 10 min followed by the addition of N,N-diisopropylethylamine (19 μL, 0.11 mmol). The reaction mixture was stirred for 1.5 h, concentrated and purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (7.2 mg, 20%) as an amorphous brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.57-7.56 (m, 2H), 7.53 (d, J=5.4 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 7.32-7.30 (m, 2H), 7.16 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.71 (q, J=4.6 Hz, 1H), 2.82 (s, 3H), 1.62 (d, J=7.0 Hz, 3H); ESI MS m/z 415 [C₂₀H₁₈N₂O₄S₂+H]⁺; HPLC >99%, t_(R)=10.18 min.

Example 175 9-[4-(2-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 9-[4-(2-aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (800 mg, 1.8 mmol) was reacted with tribromoborane (10 mL) to afford the desired product (520 mg, 88%) as an off-white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.78 (s, 1H), 9.20 (s, 1H), 7.88 (br s, 2H), 7.69 (d, J=5.4 Hz, 1H), 7.41-7.36 (m, 3H), 7.22 (d, J=8.1 Hz, 2H), 7.15 (d, J=8.9 Hz, 1H), 5.88 (d, J=5.4 Hz, 1H), 3.21-3.14 (m, 2H), 3.01-2.98 (m, 2H); ESI MS m/z 337 [C₁₉H₁₆N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=7.72 min.

Example 176 9-[4-(2-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 9-[4-(2-aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one (800 mg, 1.8 mmol) was reacted with tribromoborane (10 mL) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (520 mg, 88%) as an off-white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 11.78 (s, 1H), 9.20 (s, 1H), 7.88 (br s, 2H), 7.69 (d, J=5.4 Hz, 1H), 7.41-7.36 (m, 3H), 7.22 (d, J=8.1 Hz, 2H), 7.15 (d, J=8.9 Hz, 1H), 5.88 (d, J=5.4 Hz, 1H), 3.21-3.14 (m, 2H), 3.01-2.98 (m, 2H); ESI MS m/z 337 [C₁₉H₁₆N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=7.72 min.

Example 112 8-Hydroxy-9-{4-[4-(methylsulfonyl)piperazin-1-yl]phenyl}thieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, 8-methoxy-9-{4-[4-(methylsulfonyl)piperazin-1-yl]phenyl}thieno[2,3-c]quinolin-4(5H)-one (32 mg, 0.068 mmol) was reacted with tribromoborane (1.0 mL) to afford the desired product (5.2 mg, 17%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.58 (d, J=5.4 Hz, 1H), 7.37 (d, J=8.9 Hz, 1H), 7.20 (s, 4H), 7.15 (d, J=8.9 Hz, 1H), 6.16 (d, J=5.4 Hz, 1H), 3.44-3.43 (m, 8H), 2.92 (s, 3H); ESI MS m/z 456[C₂₂H₂₁N₃O₄S₂+H]⁺; HPLC >99%, t_(R)=10.47 min.

Example 95 9-[4-(Aminomethyl)phenyl]-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one

Following General Procedure F, tert-butyl 4-(8-methoxy-2-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (80 mg, 0.17 mmol) was reacted with tribromoborane (2.0 mL) to afford the desired product (20 mg, 37%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.63 (d, J=8.9 Hz, 2H), 7.40-7.37 (m, 3H), 7.15 (d, J=8.1 Hz, 1H), 5.76 (s, 1H), 4.28 (s, 2H), 2.33 (s, 3H); ESI MS m/z 337 [C₁₉H₁₆N₂O₂S+H]⁺; HPLC >99%, t_(R)=5.91 min.

Example 84 8-Hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one

Following General Procedure B, 9-bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one (80 mg, 0.20 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enylcarbamate (90 mg, 0.29 mmol) to afford the desired product (140 mg, 23%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 8.01-7.98 (m, 2H), 7.35 (d, J=8.9 Hz, 1H), 7.12 (d, J=8.9 Hz, 1H), 5.80 (s, 1H), 4.01-3.91 (m, 2H), 3.63-3.60 (m, 2H), 2.88-2.84 (m, 1H), 2.57-2.53 (m, 1H); ESI MS m/z 299 [C₁₆H₁₄N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=6.70 min.

Example 77 N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]methanesulfonamide

Following General Procedure F, N-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]methanesulfonamide (40 mg, 0.10 mmol) was reacted with tribromoborane (3.0 mL) to afford the desired product (3.8 mg, 10%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.61 (d, J=5.4 Hz, 1H), 7.44-7.43 (m, 2H), 7.39 (d, J=5.4 Hz, 1H), 7.29-7.27 (m, 2H), 7.16 (d, J=8.4 Hz, 1H), 6.12 (d, J=5.0 Hz, 1H), 3.09 (s, 3); ESI MS m/z 387 [C₁₈H₁₄N₂O₄S₂+H]⁺; HPLC >99%, t_(R)=9.69 min.

Example 196 9-{4-[1-(Diethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, 9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (30 mg, 0.081 mmol) was reacted with formaldehyde (37% in water, 15 mg, 0.26 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (7.2 mg, 21%) as a light brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.73 (q, J=6.9 Hz, 2H), 7.58 (d, J=5.4 Hz, 1H), 7.48-7.45 (m, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.78 (q, J=4.7 Hz, 1H), 3.51-3.34 (m, 3H), 3.19-3.12 (m, 1H), 1.86 (d, J=6.9 Hz, 3H), 1.43 (t, J=7.3 Hz, 3H), 1.37 (t, J=7.3 Hz, 3H); ESI MS m/z 393 [C₂₃H₂₄N₂O₂S+H]⁺; HPLC >99% (AUC), t_(R)=8.29 min.

Example 195 9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, tert-butyl 1-[4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethylcarbamate (320 mg, 0.71 mmol) was reacted with tribromoborane (10 mL) to afford the desired product (160 mg, 59%) as a light brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.64-7.63 (m, 2H), 7.55 (d, J=5.4 Hz, 1H), 7.43-7.40 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.08 (d, J=5.4 Hz, 1H), 4.61 (q, J=6.9 Hz, 1H), 1.76 (d, J=6.9 Hz, 3H); ESI MS m/z 337 [C₁₉H₁₆N₂O₂S+H]⁺; HPLC 98.1% (AUC), t_(R)=7.63 min.

Example 194 8-Hydroxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 8-methoxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one (70 mg, 0.17 mmol) was reacted with tribromoborane (2.0 mL) to afford the desired product (43 mg, 58%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.70-7.66 (m, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.48-7.44 (m, 2H), 7.42 (d, J=8.9 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.53 (q, J=6.8 Hz, 1H), 3.45 (br s, 1H), 3.20-3.10 (m, 1H), 2.20-2.00 (m, 4H), 1.87 (d, J=6.9 Hz, 3H); ESI MS m/z 391 [C₂₃H₂₂N₂O₂S+H]⁺; HPLC >99%, t_(R)=8.21 min.

Example 272 (R)-9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following the procedure outlined for Example 460, (R)-9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (50 mg, 0.15 mmol) was reacted with formaldehyde (14 mL, 0.45 mmol) and the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (12 mg, 20%) as an off-white solid: ¹H NMR (500 MHz, CD₃OD) δ 7.71 (q, J=2.6 Hz, 2H), 7.59 (d, J=5.4 Hz, 1H), 7.48 (t, J=7.5 Hz, 2H), 7.43 (d, J=8.9 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 6.02 (d, J=5.4 Hz, 1H), 4.66 (q, J=7.1 Hz, 1H), 2.97 (s, 3H), 2.87 (s, 3H), 1.86 (d, J=7.0 Hz, 3H); ESI MS m/z 365 [C₂₁H₂₀N₂O₂S+H]⁺; HPLC 97.1% (AUC), t_(R)=8.57 min.

Example 262 8-Hydroxy-9-{4-[1-(piperidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, 8-methoxy-9-{4-[1-(piperidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one (40 mg, 0.096 mmol) was reacted with tribromoborane (1.0 mL) to afford the desired product (4.9 mg, 13%) as a yellow solid: ¹H NMR (500 MHz, CD₃OD) δ 7.73 (d, J=8.4 Hz, 1H), 7.68 (d, J=7.8 Hz, 1H), 7.58 (d, J=5.5 Hz, 1H), 7.48-7.42 (m, 3H), 7.19 (d, J=8.9 Hz, 1H), 6.01 (d, J=5.4 Hz, 1H), 4.60 (q, J=4.5 Hz, 1H), 3.79 (d, J=12.0 Hz, 1H), 3.50 (d, J=11.7 Hz, 1H), 3.02 (t, J=11.3 Hz, 1H), 2.89 (t, J=6.0 Hz, 1H), 2.09-1.72 (m, 8H), 1.55-1.45 (m, 1H); ESI MS m/z 405 [C₂₄H₂₄N₂O₂S+H]⁺; HPLC 95.0% (AUC), t_(R)=7.83 min.

Example 261 2-[2-Fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile

Following General Procedure F, 2-[2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile (42 mg, 1.2 mmol) was reacted with tribromoborane (12 mL, 12 mmol) to afford the desired product (22 mg, 55%) as a light brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.65 (m, 2H), 7.42 (d, J=8.9 Hz, 1H), 7.19-7.14 (m, 3H), 6.16 (d, J=5.5 Hz, 1H), 4.07 (s, 2H); ESI MS m/z 351 [C₁₉H₁₁FN₂O₂S+H]⁺; HPLC 97.1% (AUC), t_(R)=13.67 min.

Example 81 2-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]acetonitrile

Following General Procedure B, 9-bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one (50 mg, 0.12 mmol) was reacted with 4-(cyanomethyl)phenylboronic acid (26 mg, 0.18 mmol) to afford the TBS protected intermediate which was treated with aqueous lithium hydroxide to afford the desired product (20 mg, 50%) as an off-white solid: ¹H NMR (500 MHz, DMSO-d₆) δ 9.28 (s, 1H), 7.73 (d, J=5.4 Hz, 1H), 7.50 (d, J=8.1 Hz, 2H), 7.38 (d, J=8.9 Hz, 1H), 7.29 (d, J=8.1 Hz, 2H), 7.18 (m, 1H), 5.90 (d, J=5.4 Hz, 1H), 4.19 (s, 2H); ESI MS m/z 333 [C₁₉H₁₂N₂O₂S+H]⁺; HPLC 96.2% (AUC), t_(R)=12.07 min.

Example 346 9-{4-[1-(Dimethylamino)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one

To a solution of 9-{4-[1-(dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (350 mg, 1.0 mmol) in anhydrous THF (20 mL) at 0° C. was added sodium hydride (60 wt %, 160 mg, 5.0 mmol) and the reaction mixture was heated to 60° C. for 1 h. The reaction mixture was cooled to 0° C. and trifluoro-N-phenyl-N-[(trifluoromethyl)sulfonyl]methanesulfonamide (450 mg, 1.1 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was quenched with satd. aq. ammonium chloride and the layers were separated. The aqueous layer was extracted with 3:1 chloroform/isopropanol and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude triflate (400 mg) as a brown solid. The crude triflate was dissolved in anhydrous DMF (30 mL) was degassed for 10 min followed by the addition of triethylamine (1.7 mL, 12 mmol), 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium(II) (70 mg, 0.080 mmol), and formic acid (0.3 mL, 8.00 mmol). The reaction mixture was heated at 100° C. for 24 h, cooled, concentrated, and the residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (60 mg, 21% for two steps) as a white solid: ¹H NMR (500 MHz, CDCl₃) δ 12.00 (s, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.51 (t, J=7.7 Hz, 1H), 7.45-7.42 (m, 3H), 7.35-7.34 (m, 2H), 7.16 (d, J=7.2 Hz, 1H), 6.30 (d, J=5.4 Hz, 1H), 3.45 (d, J=6.3 Hz, 1H), 2.32 (s, 6H), 1.50 (d, J=6.6 Hz, 3H); ESI MS m/z 349 [C₂₁H₂₀N₂OS+H]⁺; HPLC 98.5% (AUC), t_(R)=10.86 min.

Example 461 9-{4-[(tert-Butoxycarbonylamino)methyl]phenyl}-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl Trifluoromethanesulfonate

To a solution of tert-butyl 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (150 mg, 0.36 mmol) in THF (3 mL) at 0° C. was added sodium hydride (60 wt %, 18 mg, 0.44 mmol) and the reaction mixture was stirred at 0° C. for 1 h. N-Phenyl-bis(trifluoromethanesulfonimide) (160 mg, 0.44 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was quenched with water and the aqueous layer was extracted with methylene chloride. The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and the residue was purified by column chromatography (silica, methanol/methylene chloride gradient) to afford the desired product (200 mg, 98%): ESI MS m/z 555 [C₂₄H₂₁F₃N₂O₆S₂+H]⁺.

Example 462 tert-Butyl 4-(8-Cyano-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate

A solution of 9-{4-[(tert-butoxycarbonylamino)methyl]phenyl}-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl trifluoromethanesulfonate (176 mg, 0.320 mmol), zinc chloride (75 mg, 0.640 mmol), 1,1′-bis(diphenylphosphino)ferrocene (18 mg, 0.032 mmol), and tris(dibenzylideneacetone)dipalladium(0) (15 mg, 0.016 mmol) in anhydrous DMF (4 mL) was heated at 130° C. for 3 h. The reaction mixture was cooled, quenched with water and the resulting precipitate was filtered and purified by column chromatography (silica, methanol/methylene chloride gradient) to afford the desired product (120 mg, 87%) as a brown solid: ESI MS m/z 432 [C₂₄H₂₁N₃O₃S+H]⁺.

Example 326 9-[4-(Aminomethyl)phenyl]-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile Hydrochloride

Following General Procedure D-3, tert-butyl 4-(8-cyano-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (10 mg, 0.023 mmol) was reacted with 4 N HCl (3 mL) to afford the desired product (7.4 mg, 74%) as a dark brown solid: ¹H NMR (500 MHz, CD₃OD) δ 7.89 (d, J=8.6 Hz, 1H), 7.74 (t, J=9.5 Hz, 2H), 7.65 (dd, J=14.4, 7.0 Hz, 2H), 7.55-7.53 (m, 2H), 6.08 (d, J=5.4 Hz, 1H), 4.32 (s, 2H); ESI MS m/z 330 [C₁₉H₁₃N₃OS−H]⁻; HPLC 98.3% (AUC), t_(R)=9.36 min.

Example 627 (S)-4-benzyl-3-(2-(4-bromo-2-fluorophenyl)acetyl)oxazolidin-2-one

To a solution of (2-(4-bromo-2-fluorophenyl)acetic acid) (3 g, 13 mmol) and triethylamine (2.5 mL, 14 mmol) in toluene (50 mL) at 0° C. was added trimethylacetyl chloride (6.1 mL, 65 mmol) dropwise. After 10 mins the reaction mixture was cooled to −78° C. In a separate flask, to a solution of (S-(+)-4-benzyl-2-oxazolidinone (2.5 g, 14 mmol) in tetrahydrofuran (50 mL) at −78° C. was added LiHMDS (1 M in hexane, 17 mL, 17 mmol)) until yellowish color persisted. After 10 mins the resulting solution was transferred through a cannula into the suspension of mixed anhydride prepared as described above. The reaction mixture was allowed to reach rt over the period of 4 h, then diluted with saturated aqueous sodium bisulfate (ca. 20 mL), and extracted with ethyl acetate (ca. 100 mL). The extract was washed with brine (2×50 mL), dried over sodium sulfate, and evaporated under vacuum. Flash chromatography of the residue followed by trituration (hexanes) afforded the desired product (2.1 g, 42%) as white solid. ESI MS m/z 393 [C₁₈H₁₅BrFNO₃+H]⁺

Example 628 (R)-4-benzyl-3-(2-(4-bromo-2-fluorophenyl)acetyl)oxazolidin-2-one

Following the procedure outlined for Example 627, (2-(4-bromo-2-fluorophenyl)acetic acid) (10.8 g, 30.7 mmol) reacted with (S)-(+)-4-benzyl-2-oxazolidinone (5.44 g, 30.7 mmol) to obtain the desired product (4.5 g, 36%) as white solid. ESI MS nm/393 [C₁₈H₁₅BrFNO₃+H]⁺

Example 629 (S)-4-benzyl-3-((S)-2-(4-bromo-2-fluorophenyl)propanoyl)oxazolidin-2-one

To a solution of (S)-4-benzyl-3-(2-(4-bromo-2-fluorophenyl)acetyl)oxazolidin-2-one (3.6 g, 9.2 mmol) in THF (40 mL) was added a solution of methyl iodide (1 M solution in toluene, 9.6 mL, 9.6 mmol). The mixture was cooled to −78° C. and a solution of sodium bis(trimethylsilyl)amide (1 M in THF, 9.6 mL, 9.6 mmol) was added dropwise. The resultant dark red mixture was stirred for 15 min at ca. −78° C. and allowed to warm up to room temperature. After 3.5 h the reaction mixture was diluted with saturated aqueous sodium bisulfate (ca. 20 mL), and extracted with ethyl acetate (1×50 mL). The extract was washed with brine (2×50 mL), dried over sodium sulfate, and evaporated under vacuum. Flash chromatography of the residue afforded the desired product (1.7 g, 45%) as light yellow solid: ESI MS m/z 407 [C₁₉H₁₇BrFNO₃+H]+

Example 630 (R)-4-benzyl-3-((R)-2-(4-bromo-2-fluorophenyl)propanoyl)oxazolidin-2-one

Following the procedure outlined for Example 628, (R)-4-benzyl-3-(2-(4-bromo-2-fluorophenyl)acetyl)oxazolidin-2-one (4.6 g, 12 mmol) was reacted with methyl iodide (1M solution in toluene, 12.3 mL, 12.3 mmol) to obtain the desired product (3.0 g, 60%) as light yellow solid: ESI MS m/z 407 [C₁₉H₁₇BrFNO₃+H]⁺

Example 631 (S)-2-(4-bromo-2-fluorophenyl)propan-1-ol

To a solution of ((S)-4-benzyl-3-((S)-2-(4-bromo-2-fluorophenyl)propanoyl)oxazolidin-2-one) (1.7 g, 4.2 mmol) in THF (12 mL) was added a solution of sodium borohydride (700 mg, 21 mmol) in water (2 mL). The reaction mixture was stirred for 3 h at room temperature. The excess hydride was quenched by slow addition of aqueous hydrochloric acid (1 N, ca. 2.9 mL). The mixture was further diluted with water (10 mL) and extracted with ethyl acetate (1×30 mL). The combined organics were washed with brine (2×10 mL), dried over sodium sulfate, and evaporated under vacuum. The residue was purified by flash chromatography of the residue afforded the desired product (0.8 g, 82%) as light yellow oil: ESI MS m/z 234 [C₉H₁₀BrFO+H]⁺

Example 632 (R)-2-(4-bromo-2-fluorophenyl)propan-1-ol

Following the procedure outlined for Example 630, (R)-4-benzyl-3-((R)-2-(4-bromo-2-fluorophenyl)propanoyl)oxazolidin-2-one (3 g, 7.4 mmol) was reacted with sodium borohydride (1.2 g, 37 mmol) to obtain the desired product (1.5 g, 87%) as light yellow oil; ESI MS m/z 234 [C₁₁H₁₀BrFO+H]⁺

Example 633 (S)-2-(2-(4-bromo-2-fluorophenyl)propyl)isoindoline-1,3-dione

To a solution of (S)-2-(4-bromo-2-fluorophenyl)propan-1-ol (800 mg, 3.43 mmol), phthalimide (554 mg, 3.77 mmol), and triphenylphosphine (1.34 g, 5.14 mmol) in THF (2 mL) was added DIAD (1 mL, 5.14 mmol) dropwise. The reaction mixture was stirred at room temperature for 18 h and evaporated under vacuum. Flash chromatography of the residue afforded the desired product (1 g, 81%) as a white solid ESI MS m/z 363 [C₁₇H₁₃BrFNO₂+H]⁺

Example 634 (R)-2-(2-(4-bromo-2-fluorophenyl)propyl)isoindoline-1,3-dione

Following the procedure described for Example 633, (R)-2-(4-bromo-2-fluorophenyl)propan-1-ol (1.5 mg, 6.4 mmol) was reacted with phthalimide (1.0 mg, 7.008 mmol) to obtain the desired product (1.6 g, 69%) as a white solid: ESI MS m/z 363 [C₁₇H₁₃BrFNO₂+H]⁺

Example 635 (S)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate

To a solution of(S)-2-(2-(4-bromo-2-fluorophenyl)propyl)isoindoline-1,3-dione) (1.0 g, 2.8 mmol) in toluene (10 mL) was added hydrazine (1.3 mL, 41.5 mmol) dropwise. The reaction mixture was heated at 80-90° C. for 1 h and cooled to room temperature. The supernatant was decanted, and the residual solid was washed with toluene. The combined solution was evaporated under vacuum, dissolved in DCM (10 mL) and cooled to 0° C. Next, Boc₂O (870 mg, 4 mmol) and Et₃N (0.5 mL, 4 mmol) were added and the reaction mixture stirred for 30 min at room temperature. The reaction mixture diluted with DCM (20 mL) and washed with 1N HCl (1×10 mL), water (1×20 mL) followed by brine (1×10 mL), dried over sodium sulfate, and evaporated under vacuum to afford the desire product (860 mg, 99%) which was taken to next step without further purification. ESI MS m/n 333 [C₁₄H₁₉BrFNO₂+H]⁺

The next step carried out following the procedure G (Scheme II): (S)-tert-butyl 2-(4-bromo-2-fluorophenyl)propylcarbamate (860 mg, 2.66) was reacted with KOAc (833 mg, 8.5 mmol), Pd(dppf)Cl₂ (200 mg, 0.26 mmol) and bis(pinacolato)diboron (863 mg, 3.4 mmol) to afford (S)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate as a colourless paste (900 mg, 89%): ESI MS m/z 380 [C₂₀H₃₁BFNO₄+H]⁺

Example 636 (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate

Followed the procedure outlined for Example 635 (R)-2-(2-(4-bromo-2-fluorophenyl)propyl)isoindoline-1,3-dione) (1.6 g, 4.42 mmol) was reacted with hydrazine (2.1 g, 66 mmol), Boc₂O (2.0 g, 8.8 mmol) followed by bis(pinacolato)diboron (1.0 g, 4.0 mmol) to obtain the desired product (1.1 g, 80%) as a colourless paste: ESI MS m/z 380 [C₂₀H₃₁BFNO₄+H]⁺

Example 637 (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl(methyl)carbamate

Following the procedure described for Example 647, (R)-tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (400 mg, 1 mmol) was reacted with methyl iodide (1M solution in toluene, 2 mL, 2 mmol) and NaHMDS (1 M solution, 2 mL, 2 mmol) to afford the desired product (330 mg, 82%) as viscous mass. ESI MS m/z 394 [C₂₁H₃₈BFNO₄+H]⁺

Example 638 tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate

Following the procedure described for Example 647, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (5.6 g, 23 mmol) was reacted with iso propyl iodide (4 g, 24 mmol) NaHMDS (1 M solution, 24 m L, 24 mmol) to afford the desired product (2.1 g, 23%) as viscous mass. ESI MS not 390 [C₂₂H₃₆BNO₄+H]⁺.

Example 639 tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutylcarbamate

Following the procedure described for Example 647, 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (1.7 g, 6.5 mmol) was reacted with iso propyl iodide (1.1 g, 6.8 mmol) NaHMDS (1 M solution, 7.1 mL, 7.1 mmol) to afford the desired product (0.65 g, 24%) as viscous mass. ESI MS m/z 408 [C₂₂H₃₆FBNO₄+H]⁺

Example 640 tert-butyl 2-cyclopentyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate

Following the procedure described for Example 647, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (1.7 g, 7.16 mmol) was reacted with cyclopentyl iodide (1 M solution in toluene, 7.16 mL, 7.16 mmol) and NaHMDS (M solution, 7.16 mL, 7.16 mmol) to afford the desired product (1.6 g, 53%) as viscous mass. ESI MS m/z 415 [C₂₄H₃₈BNO₄+H]⁺.

Example 641 tert-butyl methyl(3-methyl-2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)carbamate

Example 642

Following the procedure described for Example 647, tert-butyl 3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (400 mg, 1 mmol) was reacted with methyl iodide (1M solution in toluene, 2 mL, 2 mmol) and NaHMDS (1 M solution, 2 mL, 2 mmol) to afford the desired product (350 mg, 84%) as viscous mass. ESI MS m/z 403 [C₂₃H₃₈BNO₄+H]⁺.

Example 643 tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutyl(methyl)carbamate

Following the procedure described for Example 647, tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutylcarbamate (650 mg, 1.6 mmol) was reacted with methyl iodide (1M solution in toluene, 3.2 mL, 3.2 mmol) and NaHMDS (1 M solution, 4.8 mL, 4.8 mmol) to afford the desired product (650 mg, 94%) as viscous mass. ESI MS m/z 421 [C₂₃H₃₈FBNO₄+H]⁺

Example 644 tert-butyl 3-(4-bromophenyl)piperidine-1-carboxylate

To a solution of 3-(4-bromophenyl)pyridine (0.4 g, 1.68 mmol) and HCl (1.0 N solution in water, 1.7 mL, 1.7 mmol) in MeOH (20 mL) was added PtO₂ (0.5 g) and stirred for 24 h at room temperature under H₂ atmosphere (50 psi) in a Parr hydrogenation apparatus. The mixture was filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting white solid was dissolved in EtOAc (50 mL) and washed with 1 N NaOH (10 mL). The aqueous phase was extracted with EtOAc (3×50 mL), and the combined organic phase was dried (Na₂SO₄). Evaporation of the solvent gave a white solid which was redissolved in DCM and added Boc₂O followed by Et₃N at 0° C. After stirring the reaction mixture for 1 h at room temperature diluted with DCM and washed sequentially with 1 N HCl, water and brine, dried over sodium sulfate, and evaporated under vacuum. Flash chromatography of the residue afforded the desired product as viscous mass (350 mg, 61%) ESI MS m/z 341 [C₁₆H₂₂BrNO₂+H]⁺.

Example 645 tert-butyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate

General Procedure G, tert-butyl 3-(4-bromophenyl)piperidine-1-carboxylate (350 mg, 1) was reacted with bis(pinacolato)diboron (275, 1.2 mmol) to to afford the desired product (190 mg, 48%) as a viscous mass: ESI MS m/z 388 [C₂₂H₃₄BNO₄+H]⁺.

Example 646 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile

General Procedure G, tert-butyl 3-(4-bromophenyl)piperidine-1-carboxylate (350 mg, l) was reacted with bis(pinacolato)diboron (275, 1.2 mmol) to to afford the desired product (190 mg, 48%) as a viscous mass: ESI MS m/z 388 [C₂₂H₃₄BNO₄+H]⁺.

Example 647 N-methyl(R)-tert-butyl methyl(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)carbamate

To a solution of (R)-tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamate (1.0 g, 2.88 mmol) in anhydrous THF (20 mL) was cooled to 0° C. and sodium hydride (60 wt %, 330 mg, 8.64 mmol) added portion wise. The mixture was stirred for min and then heated at 60° C. for 1 h. The flask was then cooled down to room temperature and methyl iodide (277 mL, 4.32 mmol) was added. The mixture was heated again at 60° C. for 12 h. LCMS showed completion of reaction. The reaction mixture was quenched with water and diluted with ethyl acetate (200 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (520 mg, 43%) as a white solid: ESI MS m/z 306 [C₂₀H₃₂BNO₄+H]⁺.

Example 648 (R)-tert-butyl methyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)carbamate

A solution of (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate (9.0 g, 24.93 mmol) in anhydrous THF (120 mL) was cooled to 0° C. and NaHMDS (30 mL, 29.9 mmol) was added. The mixture was stirred for 1 h, methyl iodide (1.9 mL, 29.9) in THF (40 mL) added and stirred for 14 h. The reaction mixture was quenched with water (20 mL) and diluted with ethyl acetate (250 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (6.2 g, 66%) as light yellow oil: ESI MS m/z 376 [C₂₁H₁₃NO₄+H]⁺.

Example 649 2-(4-bromophenyl)propanenitrile

To a solution of 2-(4-bromophenyl)acetonitrile (5.0 g, 25.5 mmol) in anhydrous THF (70 mL) was cooled to 0° C. and sodium hydride (60 wt %, 1.5 g, 38.3 mmol) added portion wise. The mixture was stirred at room temperature for 1 h. After which methyl iodide (1.$ mL, 28.1 mmol) was added and the mixture stirred for 14 h. The reaction mixture was carefully quenched with water at 0° C. and diluted with ethyl acetate (200 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (3.8 g, 72%) as a yellow oil: ESI MS m/z 210 [C₉H₈BrN+H]⁺.

Example 650 2-(2-chlorophenyl)propanenitrile

Following the procedure outlined for Example 649, 2-(2-chlorophenyl)acetonitrile (15 g, 98.9 mmol) was reacted with NaHMDS (118 mL, 118 mmol), and methyl iodie (7.0 mL, 108 mmol) to afford the desired product (14 g, 87%) as a brown oil: ESI MS m/z 166 [C₉H₈ClN+H]⁺.

Example 651 2-(2-chlorophenyl)propan-1-amine

To a solution of 2-(2-chlorophenyl)propanenitrile (14 g, 84.8 mmol) in toluene at 0° C. was added BH₃.THF (127, 255 mmol) and the reaction was warmed to room temperature and heated at reflux for 4 h. The reaction mixture was cooled; quenched with water, concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (13.9 g, 97%) as a reddish oil: ESI MS m/z 170 [C₉H₁₂ClN+H]⁺.

Example 652 N-(2-(4-bromo-2-chlorophenyl)propyl)-2,2,2-trifluoroacetamide

A solution of trifluoro acetic anhydride (12.8 mL, 90.1 mmol) in anhydrous methylene chloride (82 mL) was cooled to 0° C. and 2-(2-chlorophenyl)propan-1-amine (14 g, 82.8 mmol) in anhydrous methylene chloride (30 mL) was added dropwise. The mixture was stirred at room temperature for 1.5 h. The flask was again cooled to 0° C. and methane sulfonic acid (13 mL) followed by 1,3-Dibromo-5,5-Dimethylhydantoin (11.8 g, 41.4 mmol) was added in one portion. The mixture was stirred for 14 h and quenched with water (30 mL) and diluted with methylene chloride (150 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (14 g, 50%) as a yellowish oil: ESI MS m/z 344 [C₁₁H₁₀BrClF₃NO+H]⁺.

Example 653 tert-butyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate

A mixture of N-(2-(4-bromo-2-chlorophenyl)propyl)-2,2,2-trifluoroacetamide (14 g, 40.6 mmol), methanol (200 mL) and sodium hydroxide (2M, 200 mL, 81.2 mmol) was stirred at room temperature for 14 h. LCMS showed completion of the reaction. The solvent was removed, extraction with methylene chloride (200 mL) and concentrated to give an oil. The residue was dissolved in methylene chloride (100 mL) and cooled to 0° C. Triethylamine (8.3 mL, 61.0 mmol) and di-tert-butyl dicarbonate (13.3 g, 61.0 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (13.8 g, 90%) as white solid: ESI MS m/z 293 [C₁₄H₁₁BrClNO₂−56]⁺.

Example 654 tert-butyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate

Following General Procedure G, tert-butyl 2-(4-bromo-2-chlorophenyl)propylcarbamate (12.0 g, 34.5 mmol) was reacted with bis(pinacolata)diboron (13.2 g, 51.7 mmol) to afford the desired product (8.0 g, 58%) as a amorphous reddish oil: ESI MS m/z 396 [C₂₀H₃₁BClNO₄+H]⁺.

Example 655 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile

Following General Procedure G, 2-(4-bromophenyl)propanenitrile (3.5 g, 18.2 mmol) was reacted with bis(pinacolata)diboron (4.6 g, 27.1 mmol) to afford the desired product (2.5 g, 53%) as a brown solid: ESI MS m/z 258 [C₁₅H₂₀BNO₂+H]⁺.

Example 656 2-ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile

To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (2.0 g, 8.23 mmol) in DMF (40 mL) was cooled to 0° C. and sodium hydride (60 wt %, 1.2 g, 32.9 mmol) added portion wise. The mixture was stirred for 10 min and ethyl iodide (0.74 mL, 9.05 mmol) in THF (10 mL) was added. The mixture was stirred at room temperature for 12 h. The reaction mixture was quenched with water and diluted with ethyl acetate. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (950 mg, 38%) as a brown solid: ESI MS m/z 300 [C₁₈H₂₆BNO₂+H]⁺.

Example 657 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile

Following General Procedure G, 2-(4-bromophenyl)propanenitrile (5.0 g, 22.3 mmol) was reacted with bis(pinacolata)diboron (8.7 g, 33.5 mmol) to afford the desired product (5.8 g, 95%) as a white solid: ESI MS m/z 272 [C₁₆H₂₂BNO₂+H]⁺.

Example 658 (R)—N-(2-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide

A solution of trifluoro acetic anhydride (11.4 mL, 81.4 mmol) in anhydrous methylene chloride (73 mL) was cooled to 0° C. and (R)-2-phenylpropan-1-amine (10 g, 73.9 mmol) in anhydrous methylene chloride (20 mL) was added dropwise. The mixture was stirred at room temperature for 1.5 h. The flask was again cooled to 0° C. and methane sulfonic acid (12 mL) followed by 1,3-Dibromo-5,5-Dimethylhydantoin (11 g, 36.9 mmol) was added in one portion. The mixture was stirred for 14 h and quenched with water (30 mL) and diluted with methylene chloride (100 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (21 g, 91%) as a yellow solid: ESI MS m/z 310 [C₁₁H₁₁BrF₃NO+H]⁺.

Example 659 (R)-tert-butyl 2-(4-bromophenyl)propylcarbamate

A mixture of (R)—N-(2-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide (21 g, 68.3 mmol), methanol (40 mL) and sodium hydroxide (2M, 68 mL, 136 mmol) was stirred at room temperature for 14 h. LCMS showed completion of the reaction. The solvent was removed, extraction with methylene chloride (250 mL) and concentrated to give an oil. The residue was dissolved in methylene chloride (100 mL) and cooled to 0° C. Triethylamine (14 mL, 102 mmol) and di-tert-butyl dicarbonate (22 g, 102 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (19 g, 91%) as yellow oil: ESI MS m/z 257 [C₁₄H₂₀BrNO₂−56]⁺.

Example 660 (R)-tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate

Following General Procedure G, (R)-tert-butyl 2-(4-bromophenyl)propylcarbamate (19 g, 60.5 mmol) was reacted with bis(pinacolata)diboron (24 g, 94.4 mmol) to afford the desired product (22 g, 99%) as a light yellow solid: ESI MS m/z 362 [C₂₀H₃₂BNO₄+H]⁺.

Example 661 (R)—N-(1-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide

A solution of trifluoro acetic anhydride (5.7 mL, 40.7 mmol) in anhydrous methylene chloride (40 mL) was cooled to 0° C. and (R)-1-phenylpropan-1-amine (5 g, 36.9 mmol) in anhydrous methylene chloride (10 mL) was added dropwise. The mixture was stirred at room temperature for 1.5 h. The flask was again cooled to 0° C. and methane sulfonic acid (6.3 mL) followed by 1,3-dibromo-5,5-dimethylhydantoin (5.3 g, 18.5 mmol) was added in one portion. The mixture was stirred for 14 h and quenched with water (30 mL) and diluted with methylene chloride (50 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (8.1 g, 73%) as a white solid: ESI MS m/z 310 [C₁₁H₁₁BrF₃NO+H]⁺.

Example 662 (R)-tert-butyl 1-(4-bromophenyl)propylcarbamate

A mixture of (R)—N-(1-(4-bromophenyl)propyl)-2,2,2-trifluoroacetamide (8.1 g, 68.3 mmol), methanol (20 mL) and sodium hydroxide (2M, 15 mL, 30.6 mmol) was stirred at room temperature for 14 h. LCMS showed completion of the reaction. The solvent was removed, extraction with methylene chloride (150 mL) and concentrated to give an oil. The residue was dissolved in methylene chloride (100 mL) and cooled to 0° C. Triethylamine (2.2 mL, 15.3 mmol) and di-tert-butyl dicarbonate (3.3 g, 15.3 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (5.8 g, 70%) as off-white solid: ESI MS m/z 257 [C₁₄H₂₀BrNO₂−56]⁺.

Example 663 (R)-tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate

Following General Procedure G, (R)-tert-butyl 1-(4-bromophenyl)propylcarbamate (5.8 g, 18.4 mmol) was reacted with bis(pinacolata)diboron (7.03 g, 27.7 mmol) to afford the desired product (6.18 g, 92%) as yellow oil: ESI MS m/z 362 [C₂₀H₃₂BNO₄+H]⁺.

Example 664 tert-butyl 1-(4-bromophenyl)propan-2-ylcarbamate

To a solution of 1-(4-bromophenyl)propan-2-one (5.0 g, 23.4 mmol) in ethanol (115 mL) was added ammonia in methanol (9 N, 20.2 mL, 140 mmol) followed by Titanium isoperoxide (13.3 mL, 46.9 mmol). The mixture was heated at 50° C. overnight. The flask was cooled to 0° C. and NaBH₄ (142 mg, 3.76 mmol) was added in portions. After stirring for 1 h, NH₄OH (2 N, 4.0 mL) was added and the mixture stirred for 1 h. The white solid was filtered off and the filtrate extracted with methylene chloride. Solvent was removed and oil obtained was dissolved in methylene chloride (100 mL) and cooled to 0° C. Triethylamine (4.8 mL, 35.2 mmol) and di-tert-butyl dicarbonate (10.2 g, 46.9 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (4.2 g, 57%) as white solid: ESI MS m/z 257 [C₁₄H₂₀BrNO₂−56]⁺.

Example 665 tert-butyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamate

Following General Procedure G, tert-butyl 1-(4-bromophenyl)propan-2-ylcarbamate (8.8 g, 28.03 mmol) was reacted with bis(pinacolata)diboron (10.7 g, 42.0 mmol) to afford the desired product (10.5 g, 99%) as a brown oil: ESI MS m/z 362 [C₂₀H₃₂BNO₄+H]⁺.

Example 666 tert-butyl 2-ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate

To a solution of cyano compound (500 mg, 1.67 mmol) in toluene (10 mL) at 0° C. was added BH₃.THF (1.0 M in THF, 16 mL, 10 mmol) and the reaction was warmed to room temperature and heated at reflux for 4 h. The reaction mixture was cooled; quenched with water, concentrated. The residue was dissolved in methylene chloride (30 mL) and cooled to 0° C. Triethylamine (0.36 mL, 2.51 mmol) and di-tert-butyl dicarbonate (547 mg, 2.51 mmol) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (480 mg, 71%) as a brown solid: ESI MS m/z 404 [C₂₃H₃₈BNO₄+H]⁺.

Example 667 tert-butyl 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propylcarbamate

Following the procedure outlined for Example 666, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (5.8 g, 21.4 mmol) was reacted with BH₃.THF (1.0 M in THF, 64 mL, 64 mmol) and di-tert-butyl dicarbonate (7.0 g, 32.1 mmol) to give the desired product (6.9 g, 86%) as a white solid: ESI MS m/z 310 [C₂₁H₃₄BNO₄−56]⁺.

Example 668 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutanecarbonitrile

To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (7.0 g, 29 mmol) in THF at 0° C. was added NaHMDS (1.0 M, 120 mL, 120 mmol). After stirring for 20 min 1,3-diiodopropane (26 g, 86 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was cooled to 0° C., quenched with MeOH (5.0 mL) and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (4.0 g, 47%) as a yellow oil: ESI MS m/z 286 [C₁₇H₂₂BNO₂+H]⁺.

Example 669 (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methanamine

Following the procedure outlined for Example 666, 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutane carbonitrile (4.0 g, 14 mmol) was reacted with BH₃.THF (1.0 M in THF, 60 mL, 60 mmol) to afford the desired product (3.7 g, 91%) as a yellow oil: ESI MS m/z 288 [C₁₁H₂BNO₂+H]⁺.

Example 670 tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methylcarbamate

Following the procedure outlined for Example 463, (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)methanamine (3.7 g, 13 mmol)) was reacted with di-tert-butyl dicarbonate (3.4 g, 16 mmol) to afford the desired product (3.5 g, 71%) as a yellow oil: ESI MS m/z 388 [C₂₂H₃₄BNO₄+H]⁺.

Example 671 4-bromo-2-chloro-1-(2-nitrovinyl)benzene

To a solution of 4-bromo-2-chlorobenzaldehyde (7.5 g, 34 mmol) in nitromethane was added methylamine hydrochloride (1.3 g, 22 mmol), NaOAc (1.8 g, 22 mmol). The mixture was vigorously stirred for 18 h at room temperature. The reaction mixture was diluted with water (60 mL) and extracted with CH₂Cl₂ (3×100 mL), organic phases dried (Na₂SO₄), evaporated to afford the desired product (8.5 g, 95%) as a light yellow oil: ESI MS m/z 262 [C₈H₅BrClNO₂+H]⁺.

Example 672 2-(4-bromo-2-chlorophenyl)ethanamine

To a stirred suspension of LiBH₄ (2.0 M, 73 mL, 145 mmol) in THF (60 mL) at room temperature was added chlorotrimethylsilane (32 g, 290 mmol), dropwise over 10 min. After stirring at room temperature for 20 min, nitrogen gas was bubbled through the mixture for 5 min to remove the remaining trimethylsilane that had formed. A solution of 4-bromo-2-chloro-1-(2-nitrovinyl)benzene (9.5 g, 36.2 mmol) in THF (60 mL) was added dropwise over 10 min with stirring at room temperature. The resulting mixture was heated at reflux for 1 h. The reaction mixture was cooled in an ice bath and carefully quenched with MeOH (100 mL). The solvent was evaporated and the residue was partitioned between 20% KOH (120 mL) and CH₂Cl₂ (60 mL). The organic layer was dried, concentrated, purified by column chromatography (silica, ethyl acetate/hexanes gradient) to obtain the desired product (8.5 g, 95%) as a light yellow oil: ESI MS m/z 234 [C₈H₉BrClN+H]⁺.

Example 673 tert-butyl 4-bromo-2-chlorophenethyl carbamate

Following the procedure outlined for Example 463, 2-(4-bromo-2-chlorophenyl)ethanamine (7.5 g, 32 mmol) was reacted with di-tert-butyl dicarbonate (8.3 g, 38 mmol) to afford the desired product (9.7 g, 90%) as a white solid: ESI MS m/z 334 [C₁₃H₁₇BrCLNO₂+H]⁺.

Example 674 tert-butyl 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate

Following General Procedure G, tert-butyl 4-bromo-2-chlorophenethylcarbamate (9.6 g, 30 mmol) was reacted with bis(pinacolato)diboron (11 g, 45 mmol to afford the desired product (8.2 g, 73%) as a colorless oil: ESI MS m/z 382 [C₁₉H₂₉BCLNO₂+H]⁺.

Example 675 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile

Following the procedure outlined for Example 649, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (5.2 g, 21 mmol)) was reacted with ethyl bromide (2.6 g, 24 mmol) to afford the desired product (3.4 g, 59%) as colorless oil: ESI MS m/z 272 [C₁₆H₂₂BNO₂+H]⁺.

Example 676 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butan-1-amine

Following the procedure outlined for Example 666, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile (3.4 g, 12.5 mmol) was reacted with BH₃.THF (1.0 M in THF, 64 mL, 64 mmol) to afford the desired product (3.2 g, 93%) as light yellow oil: ESI MS m/z 276 [C₁₆H₂₆BNO₂+H]⁺.

Example 677 (1-(4-bromophenyl)cyclopropyl)methanamine

Following the procedure outlined for Example 666, 1-(4-bromophenyl)cyclopropane carbonitrile (2.0 g, 9.0 mmol) was reacted with BH₃.THF (1.0 M in THF, 50 mL, 50 mmol) to afford the desired product (1.9 g, 94%) as a yellow oil: ESI MS m/z 226 [C₁₀H₁₂BrN+H]⁺.

Example 678 tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate

Following the procedure outlined for Example 463, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butan-1-amine (2.9 g, 10.5 mmol) was reacted with di-tert-butyl dicarbonate (2.8 g, 12.6 mmol) to afford the desired product (2.4 g, 62%) as a light yellow oil: ESI MS m/z 376 [C₁₂H₃₄BNO₄+H]⁺.

Example 679 tert-butyl (1-(4-bromophenyl)cyclopropyl)methylcarbamate

Following the procedure outlined for Example 463, (1-(4-bromophenyl)cyclopropyl)methanamine (2.2 g, 9.5 mmol) was reacted with di-tert-butyl dicarbonate (2.5 g, 12 mmol) to afford the desired product (1.5 g, 52%) as a yellow oil: ESI MS m/z 326 [C₁₅H₂₀BrNO₂+H]⁺.

Example 680 tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methylcarbamate

Following General Procedure G, tert-butyl (1-(4-bromophenyl)cyclopropyl)methyl carbamate (1.3 g, 4.0 mmol) was reacted with bis(pinacolato)diboron (1.55 g, 6.1 mmol) to afford the desired product (1.8 g, 60%) as a colorless oil: ESI MS m/z 374 [C₂₁H₃₂BNO₄+H]⁺.

Example 463 tert-Butyl 4-Bromophenethylcarbamate

To a solution of 2-(4-bromophenyl)ethanamine (3.0 g, 15 mmol) in methylene chloride (75 mL) at 0° C. was added triethylamine (2.5 mL, 18 mmol) and di-tert-butyl dicarbonate (3.9 g, 18 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated and the residue was triturated with acetonitrile and filtered to afford the desired product (3.5 g, 75%) as a yellow solid: ESI MS m/z 301 [C₁₃H₁₈BrNO₂+H]⁺.

Example 464 tert-Butyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate

Following General Procedure G, tert-butyl 4-bromophenethylcarbamate (1.3 g, 4.3 mmol) was reacted with bis(pinacolato)diboron (1.3 g, 5.1 mmol) to afford the desired product (1.1 g, 70%) as a light brown solid: ESI MS m/z 348 [C₁₉H₃₀BNO₄+H]⁺.

Example 465 tert-Butyl 4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethylcarbamate

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (780 mg, 2.5 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbamate (1.5 g, 4.3 mmol) to afford the desired product (1.0 g, 90%) as a brown solid: ESI MS m/z 451 [C₂₅H₂₆N₂O₄S+H]⁺.

Example 466 2-[4-(3-Bromopropoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

To a solution of 4-(3-bromopropoxy)phenylboronic acid (1.0 g, 3.9 mmol) in diethyl ether (40 mL) was added pinacol (1.4 g, 12 mmol) and the reaction mixture was stirred for 18 h and concentrated to afford the desired product (1.5 g, crude) as a light brown oil which carried onto the next step without further purification: ESI MS m/z 247 [C₁₅H₂₂BBrO₃−94]⁺.

Example 467 N¹,N¹-Diethyl-N²-{3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propyl}ethane-1,2-diamine

A solution of 2-[4-(3-bromopropoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (500 mL, 2.02 mmol), N¹,N¹-diethylethane-1,2-diamine (0.87 mL, 6.1 mmol), and potassium carbonate (550 mg, 4.0 mmol) in acetonitrile (15 mL) was heated to 50° C. for 3 h. The reaction mixture was cooled, filtered and the filtrate was concentrated to afford the desired product (400 mg, 53%) as a yellow oil: ESI MS m/z 377 [C₂₁H₃₇BN₂O₃+H]⁺.

Example 468 tert-Butyl 1-(4-Bromophenyl)ethylcarbamate

Following the procedure outlined for Example 463, 1-(4-bromophenyl)ethanamine (3.0 g, 15 mmol) was reacted with di-tert-butyl dicarbonate (3.9 g, 18 mmol) to afford the desired product (4.2 g, 93%) as a white solid: ESI MS m/z 301 [C₁₃H₁₈BrNO₂+H]⁺.

Example 469 tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate

Following General Procedure G, tert-butyl 1-(4-bromophenyl)ethylcarbamate (2.2 g, 7.3 mmol) was reacted with bis(pinacolata)diboron (3.9 g, 11 mmol) to afford the desired product (1.3 g, 53%) as an off-white solid: ESI MS m/z 247 [C₁₉H₃₀BNO₄+H]⁺.

Example 470 (S)-tert-Butyl 1-(4-Bromophenyl)ethylcarbamate

Following the procedure outlined for Example 463, (S)-1-(4-bromophenyl)ethanamine (500 mg, 2.5 mmol) was reacted with di-tert-butyl dicarbonate (650 mg, 3.0 mmol) to afford the desired product (640 mg, 82%) as a white solid: ESI MS m/z 247 [C₁₃H₁₈BrNO₂+H]⁺.

Example 471 (S)-tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate

Following General Procedure G, (S)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (630 mg, 2.1 mmol) was reacted with bis(pinacolato)diboron (1.1 g, 3.1 mmol) to afford the desired product (320 mg, 44%) as a brown solid: ESI MS m/z 347 [C₁₉H₃₀BNO₄-Boc]⁺.

Example 472 2-[2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile

Following General Procedure G, 2-(4-bromo-2-fluorophenyl)acetonitrile (4.0 g, 19 mmol) was reacted with bis(pinacolato)diboron (7.1 g, 28 mmol) to afford the desired product (2.5 g, 57%) as a brown solid: ESI MS m/z 232 [C₁₄H₁₇BFNO₂+H]⁺.

Example 473 (R)-tert-Butyl 1-(4-Bromophenyl)ethylcarbamate

Following the procedure outlined for Example 463, (R)-1-(4-bromophenyl)ethanamine (1.0 g, 5.0 mmol) was reacted with di-tert-butyl dicarbonate (1.3 g, 5.9 mmol) to afford the desired product (1.2 g, 86%) as an off-white solid: ESI MS m/z 301 [C₁₃H₁₈BrNO₂+H]⁺.

Example 474 (R)-tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate

Following General Procedure G, (R)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (1.2 g, 4.0 mmol) was reacted with bis(pinacolato)diboron (1.5 g, 6.0 mmol) to afford the desired product (1.0 g, 77%) as a colorless oil: ESI MS m/z 292 [C₁₉H₃₀BNO₄−55]⁺.

Example 475 2-Methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile

Following General Procedure G, 2-(4-bromophenyl)-2-methylpropanenitrile (1.0 g, 4.5 mmol) was reacted with bis(pinacolato)diboron (1.7 g, 6.7 mmol) to afford the desired product (980 mg, 81%) as an off-white solid: ESI MS m/z 272 [C₁₆H₂₂BNO₂+H]⁺.

Example 476 1-[2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]pyrrolidin-3-ol

A solution of 2-[4-(bromomethyl)-3-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (300 mg, 0.95 mmol), pyrrolidin-3-ol (99 mg, 1.1 mmol), and potassium carbonate (160 mg, 1.1 mmol) in acetonitrile (5 mL) was heated to 50° C. for 3 h. The reaction mixture was cooled, filtered and the filtrate was concentrated to afford the desired product (280 mg, 92%) as a red oil: ESI MS m/z 322 [C₁₇H₂₅BFNO₃+H]⁺.

Example 477 tert-Butyl 5-Bromo-2,3-dihydro-1H-inden-2-ylcarbamate

Following the procedure outlined for Example 463, 5-bromo-2,3-dihydro-1H-inden-2-amine (2.5 g, 8.5 mmol) was reacted with di-tert-butyl dicarbonate (2.8 g, 13 mmol) to afford the desired product (2.5 g, 96%) as a white solid: ESI MS m/z 313 [C₁₄H₁₈BrNO₂+H]⁺.

Example 478 tert-Butyl 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-ylcarbamate

Following General Procedure G, tert-butyl 5-bromo-2,3-dihydro-1H-inden-2-ylcarbamate (2.5 g, 8.0 mmol) was reacted with bis(pinacolato)diboron (3.0 g, 12 mmol) to afford the desired product (2.1 g, 72%) as a colorless oil: ESI MS m/z 360 [C₂₀H₃₀BNO₄+H]⁺.

Example 479 tert-Butyl 7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Following General Procedure G, tert-butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.3 g, 4.4 mmol) was reacted with bis(pinacolato)diboron (1.7 g, 6.6 mmol) to afford the desired product (1.1 g, 72%) as a colorless oil: ESI MS m/z 360 [C₂₀H₃₀BNO₄+H]⁺.

Example 480 1-(4-Bromo-2-fluorophenyl)ethanamine

To a solution of 1-(4-bromo-2-fluorophenyl)ethanone (2.0 g, 9.2 mmol) in methanol (50 mL) was added ammonia (7 N in methanol, 8.0 mL, 55 mmol) and titanium(IV) isopropoxide (5.4 mL, 18 mmol). The reaction mixture was stirred at room temperature for 18 h, cooled to 0° C. and sodium borohydride (520 mg, 14 mmol) was added. The reaction mixture was warmed to room temperature, stirred for 20 min, quenched with 2 M ammonium hydroxide and filtered. The reaction mixture was extracted with methylene chloride and the combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford the desired product (1.2 g, 63%) as an oil: ESI MS m/z 219 [C₈H₉BrFN+H]⁺.

Example 481 tert-Butyl 1-(4-Bromo-2-fluorophenyl)ethylcarbamate

Following the procedure outlined for Example 463, 1-(4-bromo-2-fluorophenyl)ethanamine (1.2 g, 5.6 mmol) was reacted with di-tert-butyl dicarbonate (1.4 g, 6.7 mmol) to afford the desired product (1.3 g, 73%) as a white solid: ESI MS m/z 219 [C₁₃H₁₇BrFNO₂+H−100]⁺.

Example 482 tert-Butyl 1-[2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate

Following General Procedure G, tert-butyl 1-(4-bromo-2-fluorophenyl)ethylcarbamate (1.3 g, 4.4 mmol) was reacted with bis(pinacolato)diboron (1.7 g, 6.6 mmol) to afford the desired product (1.5 g, 93%) as a white solid: ESI MS m/z 266 [C₁₉H₂₉BFNO₄+H−100].

Example 483 3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile

Following General Procedure G, 3-(4-bromophenyl)propanenitrile (1.0 g, 4.8 mmol) was reacted with bis(pinacolato)diboron (1.8 g, 7.1 mmol) to afford the desired product (1.1 g, 97%) as a light brown solid: ESI MS m/z 258 [C₁₅H₂₀BNO₂+H]⁺.

Example 484 N-(1-[4-Bromophenyl)ethyl]cyclopentanamine

To a solution of 1-(4-bromophenyl)ethanone (500 mg, 2.5 mmol) in ethanol (16 mL) was added cyclopentanamine (320 mg, 3.8 mmol) and the reaction mixture was heated at 50° C. for 18 h. The reaction mixture was cooled to 0° C. and sodium borohydride (140 mg, 3.8 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 30 min. The reaction mixture was quenched with 2 M aqueous ammonium hydroxide and extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford the desired product (600 mg, 90%) as a red oil: ESI MS m/z 269 [C₁₃H₁₈BrN+H]⁺.

Example 485 tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propylcarbamate

Following General Procedure G, tert-butyl 1-(4-bromophenyl)propylcarbamate (2.0 g, 6.4 mmol) was reacted with bis(pinacolato)diboron (2.4 g, 9.6 mmol) to afford the desired product (2.1 g, 93%) as a yellow solid: ESI MS m/z 305 [C₂₀H₃₂BNO₄−56]⁺.

Example 486 (S)-tert-Butyl 1-(4-Bromophenyl)ethylcarbamate

Following the procedure outlined for Example 463, (S)-1-(4-bromophenyl)ethanamine (1.0 g, 5.0 mmol) was reacted with di-tert-butyl dicarbonate (1.3 g, 6.0 mmol) to afford the desired product (1.3 g, 88%) as a white solid: ESI MS m/z 300 [C₁₃H₁₈BrNO₂+H]⁺.

Example 487 (S)-tert-Butyl 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethylcarbamate

Following General Procedure G, (S)-tert-butyl 1-(4-bromophenyl)ethylcarbamate (1.3 g, 4.4 mmol) was reacted with bis(pinacolato)diboron (1.7 g, 6.6 mmol) to afford the desired product (1.4 g, 96%) as a brown solid: ESI MS m/z 348 [C₁₉H₃₀BNO₄+H]⁺.

Example 488 N-(4-Bromobenzyl)propan-2-amine

A solution of 1-bromo-4-(bromomethyl)benzene (2.0 g, 8.0 mmol), isopropylamine (950 mg, 16 mmol) and potassium carbonate (2.2 g, 16 mmol) in acetonitrile (40 mL) was stirred at room temperature for 18 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, 0-100% methylene chloride/methanol) to afford the desired product (1.4 g, 78%) as a brown solid: ESI MS m/z 228 [C₁₀H₁₄BrN+H]⁺.

Example 489 4-({4-[(tert-Butoxycarbonylamino)methyl]piperidin-1-yl)}methyl)phenylboronic acid

Following the procedure outlined for Example 488, 4-formylphenylboronic acid (100 mg, 0.47 mmol) was reacted with tert-butyl piperidin-4-ylmethylcarbamate (70 mg, 0.47 mmol) to afford the desired product (120 mg, 77%) as a brown solid: ESI MS m/z 349 [C₁₈H₂₉BN₂O₄+H]⁺.

Example 490 (E)-tert-Butyl 1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-4-ylcarbamate

Following the procedure outlined for Example 488, (Z)-2-(3-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (210 mg, 1.1 mmol) was reacted with tert-butyl piperidin-4-ylcarbamate (640 mg, 3.2 mmol) to afford the desired product (100 mg, 30%) as a brown solid: ESI MS m/z 367 [C₁₄H₂₇BN₂O₂+H]⁺.

Example 491 1-(4-Bromophenyl)-N-methylmethanamine

Following the procedure outlined for Example 488, 1-bromo-4-(bromomethyl)benzene (1.0 g, 4.0 mmol) was reacted with methanamine (620 mg, 20 mmol) to afford the desired product (750 mg, 93%) as a brown solid: ESI MS m/z 201 [C₈H₁₀BrN+H]⁺.

Example 492 N-(4-Bromobenzyl)ethanamine

Following the procedure outlined for Example 488, 1-bromo-4-(bromomethyl)benzene (2.0 g, 8.0 mmol) was reacted with ethanamine (720 mg, 16 mmol) to afford the desired product (1.3 g, 75%) as a brown solid: ESI MS m/z 215 [C₉H₁₂BrN+H]⁺.

Example 493 (E)-2-(3-Chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A solution of (E)-3-chloroprop-1-enylboronic acid (5 g, 41 mmol), pinacol (4.9 g, 41 mmol), and magnesium sulfate (15 g, 120 mmol) in methylene chloride (100 mL) was stirred at room temperature for 18 h. The reaction mixture was filtered through silica gel and the filter cake was washed with methylene chloride. The filtrate was concentrated to afford the desired product (4.8 g, 60%) as a colorless oil: ESI MS m/z 203 [C₉H₁₆BClO₂+H]⁺.

Example 494 (E)-tert-Butyl 1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-3-ylcarbamate

Following the procedure outlined for Example 488, (E)-2-(3-chloroprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (500 mg, 2.5 mmol) was reacted with tert-butyl piperidin-3-ylcarbamate (740 mg, 3.7 mmol) to afford the desired product (320 mg, 24%) as a yellow oil: ESI MS m/z 367 [C₁₉H₃₅BN₂O₄+H]⁺.

Example 495 4-Bromo-2-fluoro-N-(2-hydroxyethyl)benzenesulfonamide

To a solution of 2-aminoethanol (0.24 mL, 4.0 mmol), and triethylamine (1.5 mL, 11 mmol) in anhydrous THF (15 mL) was added 4-bromo-2-fluorobenzene-1-sulfonyl chloride (1.0 g, 3.7 mmol) portion wise and the reaction mixture stirred at room temperature for 16 h. The reaction was filtered, the filtrate was concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (850 mg, 77%): ESI MS m/z 298 [C₈H₉BrFNO₃S+H]⁺.

Example 496 4-Bromo-N-(2-hydroxyethyl)benzenesulfonamide

To a solution of 2-aminoethanol (2.3 mL, 39 mmol), and triethylamine (16 mL, 120 mmol) in anhydrous THF (100 mL) was added 4-bromobenzene-1-sulfonyl chloride (10 g, 39 mmol) portion wise and the reaction mixture stirred at room temperature for 16 h. The reaction was filtered, the filtrate was concentrated and the residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (5.5 g, 50%): ¹H NMR (500 MHz, CDCl₃) δ 7.74 (td, J=9.0, 2.1 Hz, 2H), 7.67 (td, J=9.0, 2.1 Hz, 2H), 5.08 (s, 1H), 3.72 (t, J=5.1 Hz, 2H), 3.12 (t, J=4.8 Hz, 2H), 1.83 (s, 1H).

Example 497 N-(2-Hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide

Following General Procedure G, 4-bromo-N-(2-hydroxyethyl)benzenesulfonamide (5.0 g, 18 mmol) was reacted with bis(pinacolato)diboron (4.9 g, 20 mmol) to afford the desired product (4.2 g, 40%) as a yellow solid: ¹H NMR (300 MHz, CDCl₃) δ 7.95 (d, J=8.3 Hz, 2H), 7.85 (d, J=8.3 Hz, 2H), 5.14 (t, J=6.1 Hz, 1H), 3.68 (t, J=5.0 Hz, 2H), 3.09 (q, J=5.4 Hz, 2H), 1.36 (s, 12H).

Example 498 (S)-tert-Butyl 1-(3-Bromo-4-nitrophenyl)pyrrolidin-3-ylcarbamate

A solution of 2-bromo-4-fluoro-1-nitrobenzene (1.5 g, 6.8 mmol), (S)-tert-butyl pyrrolidin-3-ylcarbamate (1.9 g, 10 mmol), and sodium bicarbonate (1.7 g, 20 mmol) in DMSO (40 mL) was heated at 80° C. for 1 h. The reaction mixture was cooled to room temperature, poured into excess water and the resulting precipitate was filtered. The solids were washed with aqueous ammonium chloride, brine and water to afford the desired product (2.5 g, 96%) as a yellow solid: 387 [C₁₅H₂₀BrN₃O₄+H]⁺.

Example 499 (S)-tert-Butyl 1-(4-Amino-3-bromophenyl)pyrrolidin-3-ylcarbamate

A solution of (S)-tert-butyl 1-(3-bromo-4-nitrophenyl)pyrrolidin-3-ylcarbamate (2.5 g, 6.5 mmol), ammonium chloride (380 mg, 7.1 mmol), and iron (1.8 g, 32 mmol) in ethanol (20 mL) and water (10 mL) was heated to reflux for 1 h. The reaction mixture was cooled to room temperature and filtered through diatomaceous earth. The filtrate was concentrated to afford the desired product (2.3 g, >99%) as a blue solid: ESI MS m/z 357 [C₁₅H₂₂BrN₃O₂+H]⁺.

Example 500 Methyl 5-Bromothiophene-2-carboxylate

A solution of 5-bromothiophene-2-carboxylic acid (5.0 g, 24 mmol), methyl iodide (5.1 g, 30 mmol), and potassium carbonate (6.7 g, 48 mmol) in DMF (50 mL) was stirred at room temperature for 64 h. The reaction was quenched with water and the aqueous layer was extracted multiple times with ethyl acetate. The combined organic layers were washed with aqueous lithium chloride and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, ethyl acetate/hexanes gradient) to afford the desired product (4.2 g, 79%): ¹H NMR (500 MHz, CDCl₃) δ 7.54 (d, J=4.0 Hz, 1H), 7.07 (d, J=4.0 Hz, 1H), 3.87 (s, 3H).

Example 501 Methyl 5-(4-Methoxyphenyl)thiophene-2-carboxylate

Following General Procedure B, 4-methoxyphenylboronic acid (2.7 g, 18 mmol) was reacted with methyl 5-bromothiophene-2-carboxylate (2.0 g, 9.0 mmol) to afford the desired product (1.4 g, 61%): ¹H NMR (300 MHz, CDCl₃) δ 7.71 (d, J=3.9 Hz, 1H), 7.53 (td, J=9.7, 2.5 Hz, 2H), 7.14 (d, J=3.9 Hz, 1H), 6.89 (td, J=9.7, 2.5 Hz, 2H), 3.87 (s, 3H), 3.80 (s, 3H).

Example 502 5-(4-Methoxyphenyl)thiophene-2-carboxylic Acid

A solution of methyl 5-(4-methoxyphenyl)thiophene-2-carboxylate (1.4 g, 5.6 mmol), and 1 M sodium hydroxide (55 mL) in methanol (55 mL) was heated at 80° C. for 18 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (1.2 g, 93%) as an off-white solid: ESI MS m/z 325 [C₁₂H₁₀O₃S+H]⁺.

Example 503 5-(4-Methoxyphenyl)thiophene-2-carbonyl chloride

To a solution of 5-(4-methoxyphenyl)thiophene-2-carboxylic acid (0.60 g, 2.5 mmol) in toluene (4 mL) was added thionylchloride (560 mL, 7.7 mmol) and the reaction mixture was heated at 100° C. for 18 h. The reaction mixture was cooled to room temperature and concentrated to afford the desire product (642 mg, crude): ESI MS m/z 253 [C₁₂H₉ClO₂S+H]⁺.

Example 504 (S)-tert-Butyl 1-{3-Bromo-4-[5-(4-methoxyphenyl)thiophene-2-carboxamido]phenyl}pyrrolidin-3-ylcarbamate

Following Step 1 from General Procedure A, 5-(4-methoxyphenyl)thiophene-2-carbonyl chloride (640 mg, 2.5 mmol) was reacted with (S)-tert-butyl 1-(4-amino-3-bromophenyl)pyrrolidin-3-ylcarbamate (800 mg, 2.2 mmol) to afford the desired product (500 mg, 39%) as a light yellow solid: ESI MS m/z 573 [C₂₇H₃₀BrN₃O₄S+H]⁺.

Example 505 (S)-tert-Butyl 1-{3-Bromo-4-[5-(4-methoxyphenyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}thiophene-2-carboxamido]phenyl}pyrrolidin-3-ylcarbamate

A solution of (S)-tert-butyl 1-{3-bromo-4-[5-(4-methoxyphenyl)thiophene-2-carboxamido]phenyl}pyrrolidin-3-ylcarbamate (400 mg, 0.69 mmol) in THF (20 mL) was cooled to 0° C. and sodium hydride (60 wt %, 140 mg, 3.5 mmol) was added. The reaction was warmed to room temperature followed by the addition of 2-(trimethylsilyl)ethoxymethyl chloride (370 mL, 2.1 mmol) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was quenched with water and diluted with ethyl acetate. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue was purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (400 mg, 87%): ESI MS m/z 703 [C₃₃H₄₄BrN₃O₅SSi+H]⁺.

Example 506 (S)-8-(3-Aminopyrrolidin-1-yl)-2-(4-methoxyphenyl)-5-{[2-(trimethylsilyl)ethoxy]methyl}thieno[2,3-c]quinolin-4(5H)-one

Following Step 3 from General Procedure A, (S)-tert-butyl 1-{3-bromo-4-[5-(4-methoxyphenyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}thiophene-2-carboxamido]phenyl}pyrrolidin-3-ylcarbamate (210 mg, 0.29 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (15 mg, 0.029 mmol) to afford the desired product (25 mg, 14%): ESI MS m/z 622 [C₂₈H₃₅N₃O₃SSi+H]⁺.

Example 51 (S)-8-(3-Aminopyrrolidin-1-yl)-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride

Following General Procedure F, (S)-8-(3-aminopyrrolidin-1-yl)-2-(4-methoxyphenyl)-5-{[2-(trimethylsilyl)ethoxy]methyl}thieno[2,3-c]quinolin-4(5H)-one (25 mg, 0.040 mmol) was reacted with tribromoborane (38 mL, 0.40 mmol) to afford the desired product (6.4 mg, 43%) as a yellow-green solid: ¹H NMR (500 MHz, CD₃OD) δ 8.06 (s, 1H), 7.71 (d, J=8.6 Hz, 2H), 7.36 (d, J=9.0 Hz, 1H), 7.26 (s, 1H), 6.99 (d, J=8.4 Hz, 1H), 6.90 (d, J=8.5 Hz, 2H), 4.09 (s, 1H), 3.74-3.69 (m, 2H), 3.59-3.57 (m, 1H), 3.48-3.39 (m, 1H), 2.57-2.52 (m, 1H), 2.25-2.23 (m, 1H); ESI MS m/z 378 [C₂₁H₁₉N₃O₂S+H]⁺; HPLC 97.1% (AUC), t_(R)=10.89 min.

Compounds of the invention of this application that the specific procedure for producing the compound was not particularly described in the Examples above were also synthesized by the similar or analogous methods by referring to the above-mentioned general procedures for producing the present compounds, Examples and such.

Examples 507 Kinase Assay

PBK activity was determined in the presence or absence of compounds using fluorescein isothiocyanate-labeled (FITC-labeled) histone H3 peptide as a substrate. The extent of FITC-labeled histone H3 peptide phosphorylation was measured by immobilized metal ion affinity-based fluorescence polarization (IMAP) technology (Sportsman J R, et al., Assay Drug Dev. Technol. 2: 205-14, 2004) using IMAP FP Progressive Binding System (Molecular Devices Corporation). Test compounds were dissolved in DMSO at 12.5 mM and then serially diluted as the DMSO concentration in the assays to be 1%. The serially diluted compounds, 0.8 ng/micro-L PBK (Carna Biosciences) and 100 nM FITC-labeled histone H3 peptide were reacted in a reaction buffer (20 mM HEPES, 0.01% Tween-20, 0.3 mM MgCl₂, 2 mM dithiothreitol, 50 micro-M ATP, pH 7.4) at room temperature for 1 hour. The reaction was stopped by the addition of three fold assay volume of progressive binding solution. Following 0.5 hour incubation at room temperature, fluorescence polarization was measured by Wallac EnVision 2103 multilabel reader (PerkinElmer). IC50 values were calculated by nonlinear four parameter fit using SigmaPlot, version 10.0 (Systat Software, Inc.).

IC₅₀ values of the typical compounds of the present invention are shown in following table 2:

TABLE 2 IC50 (microM) ID. Compound (kinase assay) 51 (S)-8-(3-Aminopyrrolidin-1-yl)-2-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4 0.078 (5H)-one Dihydrochloride 61 8-Hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one 0.0035 65 4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzene- 0.0018 sulfonamide 72 9-[4-(Aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00063 73 9-[4-(Aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00038 Hydrochloride 77 N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl] 0.0026 methanesulfonamide 81 2-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl] 0.012 acetonitrile 84 8-Hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one 0.00078 93 9-{4-4[2-(Dimethylamino)ethyl[phenyl}-8-hydroxythieno[2,3-c]quinolin-4 0.0054 (5H)-one 95 9-[4-(Aminomethyl)phenyl]-8-hydroxy-2-methylthieno][2,3-c]quinolin-4(5H)- 0.0044 one 112 8-Hydroxy-9-{4-[4-(methylsulfonyl)piperazin-1-yl]phenyl}thieno[2,3-c] 0.012 quinolin-4(5H)-one 139 tert-Butyl 0.0094 {1-[4-(8-Methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl] piperidin-4-yl}methylcarbamate 145 9-(4-{3-[2-Diethylamino)ethylamino]propoxy}phenyl)-8-methoxythieno 0.047 [2,3-c]quinolin-4(5H)-one 152 (E)-9-[3-(4-Aminopiperidin-1-yl)prop-1-enyl]-8-methoxythieno[2,3-c] 0.031 quinolin-4(5H)-one 164 9-{4-[(Dimethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)- 0.011 one 165 9-{4-[(Dimethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0069 one 169 9-[4-(2-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one 0.022 175 9-[4-(2-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.0012 176 9-[4-(2-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.0011 Hydrochloride 184 9-{4-[(Diethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0077 one 187 8-Hydroxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)- 0.0009 one 188 8-Methoxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)- 0.0078 one 192 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0016 one Hydrochloride 191 9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0019 one 193 N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl]ethyl} 0.0037 methanesulfonamide 194 8-Hydroxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)- 0.0028 one Hydrochloride 195 9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydro- 0.00073 chloride 196 9-{4-(1-(dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0045 one Hydrochloride 210 N-(2-Bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl) 0.0113 benzenesulfonamide 212 N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl] 0.0055 methanesulfonamide 216 8-Methoxy-9-{4-[1-(pyrrolidin-1-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)- 0.021 one Hydrochloride 217 9-(4-Amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.0023 Hydrochloride 222 9-{4-[1-(Dimethylamino)ethyl]phenyl}-6-fluoro-8-methoxythieno[2,3-c] 0.082 quinolin-4(5H)-one Hydrochloride 225 9-{4-[2-(Dimethylamino)ethyl]phenyl}-6-fluoro-8-hydroxythieno[2,3-c] 0.023 quinolin-4(5H)-one 229 8-Hydroxy-9-{4-[(isopropylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)- 0.0042 one Hydrochloride 232 (S)-9-[4-(1-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one 0.0074 Hydrochloride 233 (S)-9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00081 Hydrochloride 235 9-(4-{[4-(Aminomethyl)piperidin-1-yl]methyl}-3-fluorophenyl)-8-hydroxythieno 0.00057 [2,3-c]quinolin-4(5H)-one 254 N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl] 0.003 methanesulfonamide 256 9-[4-(Aminomethyl)phenyl]-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0025 one Hydrochloride 257 9-[4-(Aminomethyl)phenyl]-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)- 0.026 one Hydrochloride 261 2-[2-Fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl] 0.015 acetonitrile 262 8-Hydroxy-9-{4-[1-(piperidin-l-yl)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)- 0.0043 one Hydrochloride 265 9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)- 0.0038 one Hydrochloride 266 9-[5-(Aminomethyl)thiophen-2-yl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00078 267 9-{4-[(Ethylamino)methyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.002 Hydrochloride 269 9-{4-[(Ethylamino)methyl]phenyl}-8-methoxythieno[2,3-c]quinolin-4(5H)-one 0.006 Hydrochloride 270 9-[4-(Aminomethyl)phenyl]-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.031 one Hydrochloride 272 (R)-9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin- 0.00088 4(5H)-one Hydrochloride 273 9-[4-(3-Aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00074 Hydrochloride 274 (R)-9-[4-(1-Aminoethyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one 0.0038 Hydrochloride 275 (R)-9-[4-(1-Aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00054 Hydrochloride 276 9-[4-(2-Aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.0005 Hydrochloride 277 9-[4-(1-Amino-2-methylpropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin- 0.00067 4(5H)-one Hydrochloride 278 9-{3-Fluoro-4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl}-8-hydroxythieno 0.00097 [2,3-c]quinolin-4(5H)-one Hydrochloride 290 3-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl] 0.0032 propanenitrile 296 9-(4-Acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.023 297 N-(2-Bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c] 0.013 quinolin-9-yl)benzenesulfonamide 298 9-{3-[3-(Dimethylamino)piperidin-1-yl]propyl}-8-hydroxythieno[2,3-c] 0.083 quinolin-4(5H)-one Dihydrochloride 301 (R)-N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl] 0.0032 ethyl}methanesulfonamide 304 4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N- 0.045 dimethylbenzenesulfonamide 308 9-{4-[1-(Dimethylamino)-2-methylpropan-2-yl]phenyl}-8-hydroxythieno[2,3-c] 0.0028 quinolin-4(5H)-one Hydrochloride 313 8-Hydroxy-9-[4-(1-hydroxyethyl)phenyl]thieno[2,3-c]quinolin-4(5H)-one 0.002 314 9-{4-[1-(Cyclopentylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4 0.0028 (5H)-one Hydrochloride 319 9-[4-(2-Aminopropan-2-yl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00043 Hydrochloride 326 9-[4-(Aminomethyl)phenyl]-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8- 0.013 carbonitrile Hydrochloride 327 9-{4-[2-(Dimethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c] 0.0019 quinolin-4(5H)-one Hydrochloride 329 9-[4-(Aminomethyl)phenyl]-6-chloro-8-hydroxythieno[2,3-c]quinolin-4 0.016 (5H)-one Hydrochloride 332 N-(2-Chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl) 0.023 benzenesulfonamide 333 N-(2-Fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl) 0.031 benzenesulfonamide 334 9-[4-(2-Aminopropan-2-yl)phenyl]-6-chloro-8-hydroxythieno[2,3-c]quinolin-4 0.01 (5H)-one Hydrochloride 335 (S)-9-{4-[1-(Dimethylamino)ethyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4 0.0029 (5H)-one Hydrochloride 336 9-[4-(1-Aminopropyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00082 Hydrochloride 337 9-[4-(1-Aminopropyl)phenyl]-8-methoxythieno[2,3-c]quinolin-4(5H)-one 0.0052 Hydrochloride 338 9-{4-[1-(Diethylamino)propyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0037 one Hydrochloride 339 9-{4-[1-(Dimethylamino)propyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0019 one Hydrochloride 341 9-{4-[1-(Dimethylamino)ethyl]phenyl}-6,7-difluoro-8-hydroxythieno[2,3-c] 0.034 quinolin-4(5H)-one Hydrochloride 345 9-(2-Amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0012 one Hydrochloride 346 9-{4-[1-(Dimethylamino)ethyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one 0.0092 347 (S)-N-{1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl] 0.002 ethyl}methanesulfonamide 348 9-{4-[1-(Aminomethyl)cyclopropyl]phenyl}-8-hydroxythieno[2,3-c]quinolin-4 0.0019 (5H)-one Hydrochloride 349 9-{4-[1-(Dimethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c] 0.0019 quinolin-4(5H)-one Hydrochloride 353 8-Hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)- 0.002 one Hydrochloride 356 9-{4-[1-(Diethylamino)ethyl]-3-fluorophenyl}-8-hydroxythieno[2,3-c] 0.0036 quinolin-4(5H)-one Hydrochloride 359 9-[4-(1-Aminoethyl)-3-fluorophenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.00092 one Hydrochloride 361 1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl] 0.032 cyclopropanecarbonitrile 373 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one 0.0032 hydrochloride 379 9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c] 0.0036 quinolin-4(5H)-one hydrochloride 385 9-(4-(1-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.0039 hydrochloride 1032 9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.047 one hydrochloride 1041 9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.012 one hydrochloride 1052 (R)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)- 0.0013 one hydrochloride 1062 N-(1-bromopropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin- 0.031 9-yl)benzenesulfonamide 1064 (S)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)- 0.0025 one hydrochloride 1066 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)- 0.012 one hydrochloride 1077 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl 0.076 isopropyl carbonate hydrochloride 1081 (R)-9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4 0.0086 (5H)-one hydrochloride 1082 (S)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)- 0.0011 one hydrochloride 1087 (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c] 0.019 quinolin-4(5H)-one hydrochloride 1088 9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.016 one hydrochloride 1094 N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c] 0.01 quinolin-9-yl)benzenesulfonamide 1095 9-(4-(2-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.0013 hydrochloride 1099 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl 0.033 acetate hydrochloride 1106 9-(4-(2-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.041 hydrochloride 1111 9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.0013 hydrochloride 1112 9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4 0.0033 (5H)-one hydrochloride 1116 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c] 0.022 quinolin-4(5H)-one hydrochloride 1120 (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00088 hydrochloride 1121 (S)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one 0.0029 hydrochloride 1122 (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)- 0.0059 one hydrochloride 1123 (R)-9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.033 one hydrochloride 1126 (R)-6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno [2,3-c] 0.042 quinolin-4(5H)-one hydrochloride 1127 (S)-9-(4-(1-(ethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0014 one hydrochloride 1128 (S)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4 0.0022 (5H)-one hydrochloride 1131 (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.0013 hydrochloride 1132 (R)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c] 0.014 quinolin-4(5H)-one hydrochloride 1133 9-(4-(2-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.02 one hydrochloride 1135 (R)-6-bromo-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c] 0.03 quinolin-4(5H)-one hydrochloride 1136 9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin- 0.0086 4(5H)-one hydrochloride 1139 N-(2-chloroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl) 0.07 benzenesulfonamide 1142 9-(4-(2-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.045 one hydrochloride 1145 N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c] 0.013 quinolin-9-yl)benzenesulfonamide 1148 (S)-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)- 0.0013 one hydrochloride 1150 (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin- 0.047 4(5H)-one hydrochloride 1151 (R)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin- 0.0025 4(5H)-one hydrochloride 1154 (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c] 0.0094 quinolin-4(5H)-one hydrochloride 1157 (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4 0.018 (5H)-one hydrochloride 1159 (R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4 0.026 (5H)-one hydrochloride 1160 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.00064 one hydrochloride 1161 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)- 0.002 one hydrochloride 1162 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl) 0.013 butanenitrile 1163 (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0013 one hydrochloride 1165 6-chloro-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4 0.058 (5H)-one hydrochloride 1166 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c] 0.0044 quinolin-4(5H)-one hydrochloride 1168 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.0026 quinolin-4(5H)-one hydrochloride 1169 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.0089 quinolin-4(5H)-one hydrobromide 1172 (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c] 0.004 quinolin-4(5H)-one hydrochloride 1174 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4 0.0015 (5H)-one hydrochloride 1176 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c] 0.017 quinolin-4(5H)-one hydrochloride 1179 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin- 0.003 4(5H)-one hydrochloride 1181 (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin- 0.033 4(5H)-one hydrochloride 1187 (R)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin- 0.0013 4(5H)-one hydrochloride 1188 (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c] 0.0025 quinolin-4(5H)-one hydrochloride 1189 (R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin- 0.003 4(5H)-one hydrochloride 1190 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.0051 quinolin-4(5H)-one hydrochloride 1191 9-(4-(2-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)- 0.019 one hydrochloride 1193 9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno 0.046 [2,3-c]quinolin-4(5H)-one hydrochloride 1197 (S)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4 0.0028 (5H)-one hydrochloride 1201 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin- 0.02 4(5H)-one hydrochloride 1204 N-(1-chloropropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin- 0.015 9-yl)benzenesulfonamide 1209 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4 0.0018 (5H)-one hydrochloride 1212 9-(4-(aminomethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)- 0.016 one hydrochloride 1213 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4 0.019 (5H)-one hydrochloride 1215 (S)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c] 0.06 quinolin-4(5H)-one hydrochloride 1216 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin- 0.057 4(5H)-one hydrochloride 1217 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4 0.0047 (5H)-one hydrochloride 1218 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4 0.087 (5H)-one hydrochloride 1219 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4 0.0055 (5H)-one hydrochloride 1224 9-(4-(2-aminoethyl)-2-bromo-5-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin- 0.0064 4(5H)-one hydrochloride 1225 (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)- 0.016 one hydrochloride 1226 3-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl) 0.092 propanenitrile 1228 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.039 quinolin-4(5H)-one hydrochloride 1232 (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin- 0.016 4(5H)-one hydrochloride 1236 9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.0046 one 1239 9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)- 0.023 one hydrochloride 1242 9-(4-(2-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)- 0.037 one hydrochloride 1245 6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c] 0.045 quinolin-4(5H)-one hydrochloride 1247 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c] 0.072 quinolin-4(5H)-one hydrochloride 1251 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c] 0.055 quinolin-4(5H)-one hydrochloride 1252 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4 0.0014 (5H)-one 1253 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4 0.0041 (5H)-one hydrochloride 1254 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.0096 quinolin-4(5H)-one hydrochloride 1258 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.025 quinolin-4(5H)-one hydrochloride 1260 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c] 0.075 quinolin-4(5H)-one hydrochloride 1262 (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c] 0.012 quinolin-4(5H)-one hydrochloride 1263 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin- 0.033 4(5H)-one hydrochloride 1264 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin- 0.003 4(5H)-one hydrochloride 1265 (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c] 0.067 quinolin-4(5H)-one hydrochloride 1268 9-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin- 0.0039 4(5H)-one hydrochloride 1271 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c] 0.001 quinolin-4(5H)-one hydrochloride 1273 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c] 0.04 quinolin-4(5H)-one hydrochloride 1274 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.018 quinolin-4(5H)-one 1277 9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4 0.063 (5H)-one hydrochloride 1278 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno 0.022 [2,3-c]quinolin-4(5H)-one hydrochloride 1280 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4 0.01 (5H)-one hydrochloride 1283 9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno 0.047 [2,3-c]quinolin-4(5H)-one hydrochloride 1285 8-hydroxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno 0.05 [2,3-c]quinolin-4(5H)-one 1286 9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno 0.043 [2,3-c]quinolin-4(5H)-one hydrochloride 1288 9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno 0.02 [2,3-c]quinolin-4(5H)-one 1290 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.01 quinolin-4(5H)-one hydrochloride 1291 9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4 0.015 (5H)-one hydrochloride 1293 9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno 0.0089 [2,3-c]quinolin-4(5H)-one 1294 9-(3-fluoro-4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)-8-hydroxy-6- 0.017 methylthieno[2,3-c]quinolin-4(5H)-one 1297 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxy-6-methylthieno[2,3-c] 0.035 quinolin-4(5H)-one hydrochloride 1298 (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c] 0.032 quinolin-4(5H)-one hydrochloride 1300 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4 0.0017 (5H)-one hydrochloride 1302 8-hydroxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)- 0.075 one hydrochloride 1303 (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.014 quinolin-4(5H)-one 1304 (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.013 quinolin-4(5H)-one hydrobromide 1305 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c] 0.015 quinolin-4(5H)-one hydrochloride 1306 (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c] 0.0073 quinolin-4(5H)-one hydrochloride 1307 (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c] 0.018 quinolin-4(5H)-one hydrobromide 1309 9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one 0.00074 hydrochloride 1310 (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c] 0.054 quinolin-4(5H)-one hydrochloride 1311 (R)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6- 0.017 methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride 1312 9-(4-(1-aminobutan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)- 0.019 one hydrochloride 1315 (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6- 0.0081 methylthieno[2,3-c]quinolin4(5H)-one hydrochloride 1316 (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6- 0.033 methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride 1317 (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c] 0.022 quinolin-4(5H)-one hydrochloride 1318 (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.0036 quinolin-4(5H)-one hydrochloride 1319 (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.0034 quinolin-4(5H)-one hydrobromide 1321 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-6-chloro-8-methoxythieno[2,3-c] 0.096 quinolin-4(5H)-one hydrochloride 1324 (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno 0.032 [2,3-c]quinolin-4(5H)-one hydrochloride 1330 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4 0.0083 (5H)-one hydrochloride 1340 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-2,6-dimethylthieno[2,3-c] 0.012 quinolin-4(5H)-one hydrochloride 1341 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-2,6-dimethylthieno[2,3-c] 0.038 quinolin-4(5H)-one hydrochloride 1347 (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno 0.043 [2,3-c]quinolin-4(5H)-one hydrochloride 1352 (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.04 quinolin-4(5H)-one hydrochloride 1353 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-hydroxy-6-methylthieno[2,3-c] 0.004 quinolin-4(5H)-one hydrochloride 1354 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-methoxy-6-methylthieno 0.011 [2,3-c]quinolin-4(5H)-one hydrochloride 1364 8-hydroxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4 0.055 (5H)-one hydrochloride 1372 9-(4-(1-((dimethylamino)methyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno 0.042 [2,3-c]quinolin-4(5H)-one hydrochloride 1375 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-methoxy-6-methylthieno[2,3-c] 0.022 quinolin-4(5H)-one hydrochloride 1379 (R)-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno 0.076 [2,3-c]quinolin-4(5H)-one hydrochloride 1380 (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c] 0.085 quinolin-4(5H)-one hydrochloride 1383 (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-hydroxy-6-methylthieno[2,3-c] 0.0037 quinolin-4(5H)-one hydrochloride 1391 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c] 0.07 quinolin-4(5H)-one hydrochloride 1399 (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6- 0.058 methylthieno[2,3-c]quinolin-4(5H)-one hydrochloride 1400 9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-hydroxy-6-methylthieno[2,3-c] 0.06 quinolin-4(5H)-one hydrochloride 1401 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c] 0.051 quinolin-4(5H)-one hydrochloride 1419 2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl) 0.082 propane-1-sulfonamide

Examples 508 Western Blot Analysis

To evaluate the expression status of PBK in several cell lines, western blot analysis was performed using crude cell lysate collected from those cells. Anti-PBK antibody (clone 31, BD Biosciences) was used to visualize the expression. Breast cancer cell lines, T47D and BT-549 expressed PBK significantly although Bladder cancer cell line and HT-1197 showed no expression of PBK.

Examples 509 Cell-Based Assay

Active candidate inhibitors against PBK were evaluated for their target-specific cytotoxicity using T47D, A549, BT-549, and HT-1197 cells was used for negative control. 100 micro-L of cell suspension was seeded onto 96-well microtiter plate (ViewPlate-96FTC, PerkinElmer). The initial cell concentration of T47D, BT-549 and HT-1197 were 3,000 cells/well, 2,000 cells/well and 2,500 cells/well, respectively. Cellular growth was determined using Cell Counting Kit-8 (DOJINDO) at 72 hours after the exposure of the candidate inhibitors. IC50 was used as an indicator of the anti-proliferative activity of the inhibitors, and calculated by serial dilution method (0, 1.5625, 3.125, 6.25, 12.5, 25, 50, and 100 micro-M). Accurate IC50 values were calculated as described previously.

IC₅₀ values of the typical compounds of the present invention are shown in following table 3:

TABLE 3 IC50 IC50 IC50 IC50 (microM) (microM) (microM) (microM) ID Compound (BT549) (T47D) (A549) (HT1197) 51 (S)-8-(3-Aminopyrrolidin-1-yl)-2- 14 2.1 21 62 (4-hydroxyphenyl)thieno[2,3- c]quinolin-4(5H)-one Dihydrochloride 61 8-Hydroxy-9-(1H-indazol-6- 1.8 3.7 2.6 5.1 yl)thieno[2,3-c]quinolin-4(5H)-one 65 4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3- 3.3 4.4 100 100 c]quinolin-9-yl)benzenesulfonamide 72 9-[4-(Aminomethyl)phenyl]-8- 1.1 1.2 3.2 12 hydroxythieno[2,3-c]quinolin-4(5H)-one 73 9-[4-(Aminomethyl)phenyl]-8-hydroxy- 0.67 0.65 1.2 11 thieno[2,3-c]quinolin-4(5H)-one Hydrochloride 77 N-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3- 7.9 3.2 46 100 c]quinolin-9-yl)phenyl]methanesulfonamide 81 2-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3- 3.5 6.2 7.7 27 c]quinolin-9-yl)phenyl]acetonitrile 84 8-Hydroxy-9-(1,2,3,6-tetrahydropyridin- 5.4 4.8 11 7.1 4-yl)thieno[2,3-c]quinolin-4(5H)-one 93 9-{4-[2-(Dimethylamino)ethyl]phenyl}- 2.5 4.7 3 7 8-hydroxythieno[2,3-c]quinolin-4(5H)-one 95 9-[4-(Aminomethyl)phenyl]-8-hydroxy-2- 4.1 2.9 8.1 22 methylthieno[2,3-c]quinolin-4(5H)-one 112 8-Hydroxy-9-{4-[4-(methylsulfonyl)piperazin- 3.9 6.9 6.6 6.8 1-yl]phenyl}thieno[2,3-c]quinolin-4(5H)-one 139 tert-Butyl {1-[4-(8-Methoxy-4-oxo-4,5- 3.8 4.3 5 3.9 dihydrothieno[2,3-c]quinolin-9- yl)benzyl]piperidin-4-yl}methylcarbamate 145 9-(4-{3-[2-(Diethylamino)ethyl- 7.7 4.8 8.2 9.2 amino]propoxy}phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one 152 (E)-9-[3-(4-Aminopiperidin-1-yl) 5.8 4.4 12 6.5 prop-1-enyl]-8-methoxythieno[2,3- c]quinolin-4(5H)-one 164 9-{4-[(Dimethylamino)methyl]phenyl}-8- 2.9 4.9 2.4 7 methoxythieno[2,3-c]quinolin-4(5H)-one 165 9-{4-[(Dimethylamino)methyl]phenyl}-8- 3.2 6.2 3 6.5 hydroxythieno[2,3-c]quinolin-4(5H)-one 169 9-[4-(2-Aminoethyl)phenyl]-8-me- 2.4 4.2 3.7 6.1 thoxythieno[2,3-c] quinolin-4(5H)-one 175 9-[4-(2-Aminoethyl)phenyl]-8-hydroxy- 0.7 0.67 0.85 1.5 thieno[2,3-c]quinolin-4(5H)-one 176 9-[4-(2-Aminoethyl)phenyl]-8-hydroxy- 0.64 0.49 0.64 1.1 thieno[2,3-c]quinolin-4(5H)-one Hydrochloride 184 9-{4-[(Diethylamino)methyl]phenyl}-8- 2.9 6.1 2.7 7.1 hydroxythieno[2,3-c]quinolin-4(5H)-one 187 8-Hydroxy-9-{4-[(methyl- 1.3 1.4 1.6 2 amino)methyl]phenyl}thieno[2,3- c]quinolin-4(5H)-one 188 8-Methoxy-9-{4-[(methyl- 3.5 7.9 3.8 8 amino)methyl]phenyl}thieno[2,3- c]quinolin-4(5H)-one 192 9-(4-(1-(dimethylamino)ethyl)phenyl)-8- 0.34 0.67 0.3 0.66 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 191 9-{4-[1-(Dimethylamino)ethyl]phenyl}-8- 0.4 0.78 0.35 0.87 hydroxythieno[2,3-c]quinolin-4(5H)-one 193 N-{1-[4-(8-Hydroxy-4-oxo-4,5-di- 2.4 1.7 13 39 hydrothieno[2,3-c]quinolin-9- yl)phenyl]ethyl}methanesulfonamide 194 8-Hydroxy-9-{4-[1-(pyrrolidin-1- 0.46 1 0.49 1.2 yl)ethyl]phenyl}thieno[2,3-c]quinolin- 4(5H)-one Hydrochloride 195 9-[4-(1-Aminoethyl)phenyl]-8- 0.37 0.4 0.61 2.4 hydroxythieno[2,3-c]quinolin-4(5H)- one Hydrochloride 196 9-{4-[1-(Diethylamino)ethyl]phenyl}-8- 1.1 2.3 1 2.7 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 210 N-(2-Bromoethyl)-4-(8-hydroxy-4-oxo-4,5- 0.006 0.25 0.028 14 dihydrothieno[2,3-c]quinolin-9- yl)benzenesulfonamide 212 N-[4-(8-Hydroxy-4-oxo-4,5-dihydro- 5.5 1.4 17 40 thieno[2,3-c]quinolin-9-yl)benzyl]methane- sulfonamide 216 8-Methoxy-9-{4-[1-(pyrrolidin-1- 2.9 5.8 2.6 7.4 yl)ethyl]phenyl}thieno[2,3-c]quinolin- 4(5H)-one Hydrochloride 217 9-(4-Amino-3-hydroxyphenyl)-8- 2.8 6.8 5.6 48 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 222 9-{4-[1-(Dimethylamino)ethyl]phenyl}- 3.8 7 3.5 8.7 6-fluoro-8-methoxythieno[2,3-c]quinolin- 4(5H)-one Hydrochloride 225 9-{4-[2-(Dimethylamino)ethyl]phenyl}- 1.2 3 1.2 3.4 6-fluoro-8-hydroxythieno[2,3-c]quinolin- 4(5H)-one 229 8-Hydroxy-9-{4-[(isopropyl- 1.9 4 2.1 4.2 amino)methyl]phenyl}thieno[2,3- c]quinolin-4(5H)-one Hydrochloride 232 (S)-9-[4-(1-Aminoethyl)phenyl]-8-me- 2.1 5 2 7.3 thoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 233 (S)-9-[4-(1-Aminoethyl)phenyl]-8- 0.28 0.38 0.36 1.1 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 235 9-(4-{[4-(Aminomethyl)piperidin-1- 3.2 2.2 7.1 10 yl]methyl}-3-fluorophenyl)-8- hydroxythieno[2,3-c]quinolin-4(5H)-one 254 N-[4-(8-Hydroxy-4-oxo-4,5-dihydro- 4.8 5.2 14 32 thieno[2,3-c]quinolin-9-yl)-2-methyl- phenyl]methanesulfonamide 256 9-[4-(Aminomethyl)phenyl]-6-fluoro-8- 0.57 0.99 0.75 3.3 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 257 9-[4-(Aminomethyl)phenyl]-6-fluoro-8- 3.4 8.2 3.7 100 methoxythieno[2,3-c]quinolin-4(5H)- one Hydrochloride 261 2-[2-Fluoro-4-(8-hydroxy-4-oxo-4,5- 0.69 1.1 1.3 6.6 dihydrothieno[2,3-c]quinolin-9- yl)phenyl]acetonitrile 262 8-Hydroxy-9-{4-[1-(piperidin-1- 1.2 2.7 1 2.6 yl)ethyl]phenyl}thieno[2,3-c]quinolin- 4(5H)-one Hydrochloride 265 9-[4-(2-Aminoethyl)-3-fluorophenyl]-8- 3 5.6 4.4 7.7 methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 266 9-[5-(Aminomethyl)thiophen-2-yl]-8- 1.3 1.5 2.7 13 hydroxythieno[2,3-c]quinolin-4(5H)-one 267 9-{4-[(Ethylamino)methyl]phenyl}-8- 1.9 3.1 2 3.3 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 269 9-{4-[(Ethylamino)methyl]phenyl}-8- 3 6.9 2.3 6.7 methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 270 9-[4-(Aminomethyl)phenyl]-6-bromo-8- 0.36 0.65 0.44 2.4 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 272 (R)-9-{4-[1-Dimethylamino)ethyl]phenyl}- 0.19 0.36 0.17 0.49 8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 273 9-[4-(3-Aminopropyl)phenyl]-8-hydroxy- 3.8 2.1 6.4 5.3 thieno[2,3-c]quinolin-4(5H)-one Hydrochloride 274 (R)-9-[4-(1-Aminoethyl)phenyl]-8- 1.3 2.8 1.6 5.1 methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 275 (R)-9-[4-(1-Aminoethyl)phenyl]-8- 0.32 0.34 0.57 5.2 hydroxythieno[2,3-c] quinolin-4(5H)-one Hydrochloride 276 9-[4-(2-Aminoethyl)-3-fluorophenyl]-8- 0.81 0.57 1.3 2.1 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 277 9-[4-(1-Amino-2-methylpropan-2-yl)phenyl]- 0.53 0.74 0.69 2.1 8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 278 9-{3-Fluoro-4-[(3-hydroxypyrrolidin-1- 2.5 2.7 5 10 yl)methyl]phenyl}-8-hydroxythieno[2,3- c]quinolin-4(5H)-one Hydrochloride 290 3-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3- 0.63 0.96 0.76 2.8 c]quinolin-9-yl)phenyl]propanenitrile 296 9-(4-Acetylphenyl)-8-hydroxythieno[2,3- 5.4 7.4 3.5 14 c]quinolin-4(5H)-one 297 N-(2-Bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo- 0.21 1.2 0.47 32 4,5-dihydrothieno[2,3-c]quinolin-9- yl)benzenesulfonamide 298 9-{3-[3-(Dimethylamino)piperidin-1- 6.2 6.9 4.4 11 yl]propyl}-8-hydroxythieno[2,3- c]quinolin-4(5H)-one Dihydrochloride 301 (R)-N-{1-[4-(8-Hydroxy-4-oxo-4,5- 7.2 3 14 28 dihydrothieno[2,3-c]quinolin-9- yl)phenyl]ethyl}methanesulfonamide 304 4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3- 4.6 6.9 5.2 100 c]quinolin-9-yl)-N,N-dimethylbenzene- sulfonamide 308 9-{4-[1-(Dimethylamino)-2-methylpropan-2- 1.8 3.8 1.4 4.2 yl]phenyl}-8-hydroxythieno[2,3- c]quinolin-4(5H)-one Hydrochloride 313 8-Hydroxy-9-[4-(1-hydroxy- 1.7 3 2.6 11 ethyl)phenyl]thieno[2,3-c]quinolin- 4(5H)-one 314 9-{4-[1-(Cyclopentylamino)ethyl] 1.9 4.1 1.5 3.7 phenyl}-8-hydroxythieno[2,3-c]quinolin- 4(5H)-one Hydrochloride 319 9-[4-(2-Aminopropan-2-yl)phenyl]-8- 0.55 0.9 0.64 2.3 hydroxythieno[2,3-c]quinolin-4(5H)- one Hydrochloride 326 9-[4-(Aminomethyl)phenyl]-4-oxo-4,5- 4.3 5.9 7.9 10 dihydrothieno[2,3-c]quinoline-8- carbonitrile Hydrochloride 327 9-{4-[2-(Dimethylamino)ethyl]-3- 3.3 6.4 3.7 7.8 fluorophenyl}-8-hydroxythieno[2,3- c]quinolin-4(5H)-one Hydrochloride 329 9-[4-(Aminomethyl)phenyl]-6-chloro-8- 0.32 0.63 0.36 1.4 hydroxythieno[2,3-c]quinolin-4(5H)- one Hydrochloride 332 N-(2-Chloroethyl)-4-(8-hydroxy-4-oxo-4,5- 0.012 0.31 0.034 24 dihydrothieno[2,3-c]quinolin-9- yl)benzenesulfonamide 333 N-(2-Fluoroethyl)-4-(8-methoxy-4-oxo-4,5- 2.5 9.3 2 24 dihydrothieno[2,3-c]quinolin-9- yl)benzenesulfonamide 334 9-[4-(2-Aminopropan-2-yl)phenyl]-6-chloro-8- 0.48 1.1 0.49 1.3 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 335 (S)-9-{4-[1-(Dimethylamino)ethyl]phenyl}- 1.1 2.4 1.2 3.3 8-hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 336 9-[4-(1-Aminopropyl)phenyl]-8-hydroxy- 0.21 0.35 0.32 0.97 thieno[2,3-c]quinolin-4(5H)-one Hydrochloride 337 9-[4-(1-Aminopropyl)phenyl]-8- 1.5 3.4 1.4 3.9 methoxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 338 9-{4-[1-(Diethylamino)propyl]phenyl}-8- 2 7.1 1.8 4.5 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 339 9-{4-[1-(Dimethylamino)propyl]phenyl}-8- 0.35 0.79 0.36 0.98 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 341 9-{4-[1-(Dimethylamino)ethyl]phenyl}-6,7- 1.4 2.9 1.5 3.3 difluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)- one Hydrochloride 345 9-(2-Amino-2,3-dihydro-1H-inden-5-yl)-8- 3.1 4.4 5.7 7.1 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 346 9-{4-[1-(Dimethyl- 2.5 7.2 6.8 amino)ethyl]phenyl}thieno[2,3-c]quinolin- 4(5H)-one 347 (S)-N-{1-[4-(8-Hydroxy-4-oxo-4,5- 1 0.75 5.6 29 dihydrothieno[2,3-c]quinolin-9- yl)phenyl]ethyl}methanesulfonamide 348 9-{4-[1-(Aminomethyl)cyclopropyl]phenyl}- 0.31 3.2 0.38 1.2 8-hydroxythieno[2,3-c]quinolin-4(5H)- one Hydrochloride 349 9-{4-[1-(Dimethylamino)ethyl]-3- 0.58 1.3 0.48 1.3 fluorophenyl}-8-hydroxythieno[2,3- c]quinolin-4(5H)-one Hydrochloride 353 8-Hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7- 1.9 3.7 3.2 4.2 yl)thieno[2,3-c]quinolin-4(5H)-one Hydrochloride 356 9-{4-[1-(Diethylamino)ethyl]-3-fluoro- 1.5 3.3 1.3 3.5 phenyl}-8-hydroxythieno[2,3-c]quinolin- 4(5H)-one Hydrochloride 359 9-[4-(1-Aminoethyl)-3-fluorophenyl]-8- 0.35 0.64 0.62 4 hydroxythieno[2,3-c]quinolin-4(5H)-one Hydrochloride 361 1-[4-(8-Hydroxy-4-oxo-4,5-dihydrothieno[2,3- 0.94 2.5 0.96 2.7 c]quinolin-9-yl)phenyl]cyclopropanecarbonitrile IC50 IC50 IC50 IC50 IC50 (microM) (microM) (microM) (microM) (microM) ID Compound (BT549) (T47D) (A549) (HT1197) (22Rv1) 373 9-(4-(1-aminopropan-2-yl)phenyl)-8- 0.46 0.82 0.58 1.5 — methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 379 9-(4-(1-((dimethylamino)methyl)cyclo- 0.52 1 0.46 1.4 — propyl)phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 385 9-(4-(1-(ethylamino)ethyl)phenyl)-8- 0.8 1.8 0.94 2.6 — hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1032 9-(4-(1-aminoethyl)phenyl)-6-bromo-8- 0.27 0.53 0.3 1.2 — hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1041 9-(4-(1-aminoethyl)phenyl)-6-chloro- 0.19 0.34 0.16 0.65 — 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1052 (R)-8-hydroxy-9-(4-(1-(methyl- 0.17 0.32 0.17 0.45 — amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1062 N-(1-bromopropan-2-yl)-4-(8-hydroxy- 0.15 1.9 0.88 12 — 4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)benzenesulfonamide 1064 (S)-8-methoxy-9-(4-(1-(methyl- 1 2.2 0.89 2.9 — amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1066 9-(4-(1-aminoethyl)phenyl)-8-hydroxy- 0.065 0.13 0.12 0.34 — 6-methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1077 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5- 0.41 0.45 0.66 2.5 — dihydrothieno[2,3-c]quinolin-8- yl isopropyl carbonate hydrochloride 1081 (R)-9-(4-(1-aminoethyl)phenyl)-6- 0.086 0.17 0.1 0.39 — chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1082 (S)-8-hydroxy-9-(4-(1-(methyl- 0.36 0.6 0.43 1 — amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1087 (S)-6-chloro-8-hydroxy-9-(4-(1-(methyl- 0.23 0.5 0.26 0.66 — amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1088 9-(4-(1-aminopropyl)phenyl)-6-chloro- 0.24 0.52 0.24 0.66 — 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1094 N-(2-bromoethyl)-4-(8-hydroxy-4-oxo- 0.0071 0.29 0.028 21 — 2,3,4,5-tetrahydro-1H-cyclo- penta[c]quinolin-9-yl)benzene- sulfonamide 1095 9-(4-(2-aminopropyl)phenyl)-8- 0.81 0.54 0.95 0.93 — hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1099 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5- 0.46 0.37 0.54 1.9 — dihydrothieno[2,3-c]quinolin-8- yl acetate hydrochloride 1106 9-(4-(2-aminopropyl)phenyl)-6-chloro- 0.13 0.26 0.15 0.62 — 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1111 9-(4-(1-aminopropan-2-yl)phenyl)-8- 0.12 0.072 0.12 0.37 — hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1112 9-(4-(1-(dimethylamino)propan-2- 0.21 0.47 0.25 0.64 — yl)phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1116 9-(4-(1-(aminomethyl)cyclo- 0.098 0.17 0.12 0.54 — propyl)phenyl)-6-chloro-8-hydroxy- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1120 (S)-9-(4-(1-aminopropyl)phenyl)-8- 0.093 0.15 0.13 0.33 — hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1121 (S)-9-(4-(1-aminopropyl)phenyl)-8- 0.42 0.7 0.36 1.5 — methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1122 (R)-9-(4-(1-aminoethyl)phenyl)-8- — 0.065 0.049 0.17 0.065 hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1123 (R)-9-(4-(1-aminoethyl)phenyl)-6- 0.18 0.34 0.16 0.76 — bromo-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1126 (R)-6-chloro-9-(4-(1-(dimethyl- 0.14 0.29 0.11 0.32 — amino)ethyl)phenyl)-8-hydroxy- thieno [2,3-c]quinolin-4(5H)-one hydrochloride 1127 (S)-9-(4-(1-(ethylamino)propyl)phenyl)- 0.3 0.63 0.22 0.65 — 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1128 (S)-9-(4-(1-(dimethyl- 0.43 1 0.37 1.2 — amino)propyl)phenyl)-8-hydroxy- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1131 (R)-9-(4-(1-aminopropyl)phenyl)-8- 0.51 0.71 0.68 4.8 — hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1132 (R)-6-chloro-8-hydroxy-9-(4-(1- 0.097 0.19 0.09 0.32 — (methylamino)ethyl)phenyl)thieno [2,3- c]quinolin-4(5H)-one hydrochloride 1133 9-(4-(2-aminoethyl)phenyl)-6-chloro-8- 0.15 0.23 0.18 0.87 — hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1135 (R)-6-bromo-8-hydroxy-9-(4-(1- 0.14 0.28 0.13 0.41 — (methylamino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1136 9-(4-(1-aminopropan-2-yl)phenyl)-6- 0.032 0.057 0.035 0.18 — chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1139 N-(2-chloroethyl)-4-(8-methoxy-4-oxo- 0.017 0.2 0.023 14 — 4,5-dihydrothieno[2,3-c]quinolin- 9-yl)benzenesulfonamide 1142 9-(4-(2-aminoethyl)phenyl)-6-bromo-8- 0.17 0.25 0.21 1 — hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1145 N-(2-chloroethyl)-4-(8-hydroxy-4-oxo- 0.01 0.18 0.051 31 — 2,3,4,5-tetrahydro-1H-cyclo- penta[c]quinolin-9-yl)benzene- sulfonamide 1148 (S)-8-hydroxy-9-(4-(1-(methyl- 0.13 0.25 0.12 0.26 — amino)propyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1150 (R)-9-(4-(1-aminopropyl)phenyl)-6- — 1.1 0.51 1.3 0.88 bromo-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1151 (R)-9-(4-(1-(dimethyl- 0.39 0.85 0.32 1 — amino)propyl)phenyl)-8- hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1154 (S)-6-chloro-8-hydroxy-9-(4-(1-(methyl- 0.14 0.29 0.13 0.32 — amino)propyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1157 (R)-9-(4-(1-aminopropyl)phenyl)-8- 0.16 0.32 0.22 0.58 — hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1159 (R)-9-(4-(1-aminopropyl)phenyl)-6- 0.38 0.76 0.4 1.1 — chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1160 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.054 0.057 0.056 0.23 0.069 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1161 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.22 0.45 0.27 0.82 — 8-methoxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1162 2-(4-(8-hydroxy-4-oxo-4,5-di- 0.51 1.2 0.65 1.3 — hydrothieno[2,3-c]quinolin-9- yl)phenyl)butanenitrile 1163 (S)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.33 0.24 0.32 0.96 — 8-hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1165 6-chloro-8-hydroxy-9-(4-(2-(methyl- 0.37 0.65 0.41 1.2 — amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1166 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.013 0.026 0.017 0.12 — 6-chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1168 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- — 0.0084 0.0065 0.027 0.008 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1169 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.013 0.024 0.023 0.079 0.022 8-hydroxy-6-methylthieno [2,3- c]quinolin-4(5H)-one hydrobromide 1172 (S)-9-(4-(1-(dimethylamino)propan-2- 0.31 0.65 0.33 0.65 — yl)phenyl)-8-hydroxythieno [2,3- c]quinolin-4(5H)-one hydrochloride 1174 9-(4-(1-aminopropan-2-yl)-3- 0.16 0.12 0.27 1.2 — fluorophenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1176 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.024 0.038 0.027 0.1 — 6-bromo-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1179 9-(4-(1-aminopropan-2-yl)-3- 0.45 0.86 0.63 1.9 — fluorophenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1181 (S)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.1 0.21 0.11 0.6 — 6-chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1187 (R)-8-hydroxy-9-(4-(1-(methyl- 0.19 0.19 0.2 0.32 — amino)propan-2-yl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1188 (R)-9-(4-(1-(dimethylamino)propan-2- 0.16 0.29 0.16 0.43 — yl)phenyl)-8-hydroxythieno [2,3- c]quinolin-4(5H)-one hydrochloride 1189 (R)-8-methoxy-9-(4-(1-(methyl- 0.69 1.3 0.59 1.3 — amino)propan-2-yl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1190 9-(4-(1-aminopropan-2-yl)-3- 0.015 0.019 0.021 0.11 — fluorophenyl)-8-hydroxy-6-methyl- thieno [2,3-c]quinolin-4(5H)-one hydrochloride 1191 9-(4-(2-aminoethyl)phenyl)-8-hydroxy- 0.064 0.073 0.12 0.48 — 6-methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1193 9-(4-(1-(dimethylamino)propan-2-yl)-3- 0.14 0.24 0.13 0.33 — fluorophenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1197 (S)-8-hydroxy-9-(4-(1-(methyl- 0.43 0.54 0.62 1 — amino)propan-2-yl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1201 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.053 0.12 0.046 0.14 — 6-chloro-8-methoxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1204 N-(1-chloropropan-2-yl)-4-(8-hydroxy- 0.16 1.9 0.71 15 — 4-oxo-4,5-dihydrothieno[2,3- c]quinolin-9-yl)benzenesulfonamide 1209 9-(4-(3-(aminomethyl)pentan-3- 0.49 1 0.48 1.2 — yl)phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1212 9-(4-(aminomethyl)phenyl)-8-hydroxy- 0.12 0.2 0.15 0.63 — 6-methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1213 9-(4-(2-aminoethyl)-3-fluorophenyl)- 0.23 0.38 0.36 1.7 — 6-bromo-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1215 (S)-8-hydroxy-6-methyl-9-(4-(1- 0.14 0.26 0.15 0.5 — (methylamino)propan-2- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1216 9-(4-(2-aminoethyl)-3-fluorophenyl)- 0.21 0.46 0.28 0.64 — 8-methoxy-6-methylthieno [2,3- c]quinolin-4(5H)-one hydrochloride 1217 9-(4-(2-aminoethyl)-3-fluorophenyl)- 0.065 0.084 0.14 0.48 — 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1218 9-(4-(2-aminoethyl)-3-fluorophenyl)- 0.55 1.2 0.62 1.3 — 6-chloro-8-methoxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1219 9-(4-(2-aminoethyl)-3-fluorophenyl)- 0.1 0.18 0.17 0.88 — 6-chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1224 9-(4-(2-aminoethyl)-2-bromo-5- 0.98 0.77 0.49 1.5 — hydroxyphenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1225 (S)-9-(4-(1-aminoethyl)phenyl)-8- 0.091 0.16 0.1 0.38 — hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1226 3-(4-(8-hydroxy-6-methyl-4-oxo-4,5- 0.59 1.2 0.49 1.3 — dihydrothieno[2,3-c]quinolin-9- yl)phenyl)propanenitrile 1228 9-(4-(1-amino-2-methylpropan-2- 0.15 0.33 0.16 0.81 — yl)phenyl)-8-hydroxy-6-methyl- thieno [2,3-c]quinolin-4(5H)-one hydrochloride 1232 (S)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.037 0.062 0.041 0.2 — 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1236 9-(4-(2-amino-1-cyclopentyl- 0.51 0.8 0.46 1 — ethyl)phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1239 9-(4-(2-amino-1-cyclopentyl- 1.5 1.1 0.89 1.7 — ethyl)phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1242 9-(4-(2-aminopropyl)phenyl)-8-hydroxy- 0.11 0.15 0.12 0.42 — 6-methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1245 6-bromo-9-(3-fluoro-4-(2-(methyl- 0.72 1.3 0.85 2.5 — amino)ethyl)phenyl)-8-hydroxy- thieno[2,3-c]quinolin-4(5H)- one hydrochloride 1247 9-(4-(1-amino-2-methylpropan-2- 0.52 0.94 0.47 1.3 — yl)phenyl)-6-bromo-8-hydroxy- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1251 9-(4-(1-(aminomethyl)cyclo- 0.26 0.52 0.2 0.65 — propyl)phenyl)-8-methoxy-6-methyl- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1252 9-(4-(1-amino-3-methylbutan-2- 0.25 0.21 0.16 0.42 — yl)phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one 1253 9-(4-(1-amino-3-methylbutan-2- 1.5 0.87 0.76 1.9 — yl)phenyl)-8-methoxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1254 9-(4-(1-(aminomethyl)cyclo- 0.035 0.053 0.039 0.24 — propyl)phenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1258 9-(3-fluoro-4-(2-(methyl- 0.43 0.6 0.66 1.5 — amino)ethyl)phenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1260 9-(4-(1-amino-2-methylpropan-2- 0.43 0.93 0.5 1.7 — yl)phenyl)-6-chloro-8-hydroxy- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1262 (R)-8-hydroxy-6-methyl-9-(4-(1- 0.039 0.078 0.045 0.13 — (methylamino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1263 9-(4-(2-aminoethyl)-3-chlorophenyl)- 0.2 0.41 0.23 0.58 — 8-methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1264 9-(4-(2-aminoethyl)-3-chlorophenyl)- 0.032 0.046 0.075 0.17 — 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1265 (R)-8-methoxy-6-methyl-9-(4-(1- 0.11 0.26 0.11 0.32 — (methylamino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1268 9-(4-(2-aminoethyl)-3-chlorophenyl)- 0.077 0.12 0.13 0.38 — 6-chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1271 9-(4-(1-amino-2-methylpropan-2-yl)- 0.3 0.57 0.47 1.6 — 3-fluorophenyl)-8-hydroxy- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1273 9-(4-(1-aminopropan-2-yl)-3- 0.073 0.17 0.071 0.2 — fluorophenyl)-8-methoxy-6-methyl- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1274 9-(4-(1-amino-3-methylbutan-2- 0.066 0.098 0.045 0.18 — yl)phenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)-one 1277 9-(4-(1-aminobutan-2-yl)phenyl)-8- 0.13 0.28 0.14 0.29 — methoxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1278 9-(4-(1-amino-2-methylpropan-2-yl)-3- 0.11 0.26 0.29 0.51 — fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1280 9-(4-(1-aminopropan-2-yl)-3- 0.45 2.6 0.37 7 — chlorophenyl)-8-hydroxy- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1283 9-(4-(1-amino-3-methylbutan-2-yl)-3- 0.25 0.56 0.56 0.53 — fluorophenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1285 8-hydroxy-6-methyl-9-(4-(3-methyl-1- 0.11 0.21 0.23 0.28 — (methylamino)butan-2- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one 1286 9-(3-fluoro-4-(1-(methylamino)propan- 0.093 0.22 0.095 0.22 — 2-yl)phenyl)-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1288 9-(4-(1-amino-3-methylbutan-2-yl)-3- 0.047 0.074 0.11 0.14 — fluorophenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)-one 1290 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)- 0.025 0.044 0.021 0.096 — 8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1291 9-(4-(1-aminobutan-2-yl)phenyl)-8- 0.026 0.029 0.022 0.11 — hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1293 9-(3-fluoro-4-(1-(methyl- 0.032 0.052 0.035 0.19 — amino)propan-2-yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1294 9-(3-fluoro-4-(3-methyl-1-(methyl- 0.085 0.18 0.078 0.34 — amino)butan-2-yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one 1297 9-(4-(1-(aminomethyl)cyclo- 0.26 0.62 0.22 0.52 — butyl)phenyl)-8-methoxy-6-methyl- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1298 (R)-8-methoxy-6-methyl-9-(4-(1- 0.064 0.14 0.068 0.16 — (methylamino)propan-2- yl)phenyl)thieno [2,3-c]quinolin- 4(5H)-one hydrochloride 1300 9-(4-(l-(aminomethyl)cyclo- 0.1 0.12 0.077 0.23 — butyl)phenyl)-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1302 8-hydroxy-6-methyl-9-(4-(piperidin-3- 0.74 0.83 0.97 1.5 — yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1303 (S)-9-(4-(1-aminopropan-2-yl)-3- 0.081 0.13 0.092 0.51 — fluorophenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)-one 1304 (S)-9-(4-(1-aminopropan-2-yl)-3- — 0.12 0.099 0.34 0.074 fluorophenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)- one hydrobromide 1305 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.021 0.04 0.02 0.064 — 8-methoxy-6-methylthieno [2,3- c]quinolin-4(5H)-one hydrochloride 1306 (R)-8-hydroxy-6-methyl-9-(4-(1- — 0.035 0.02 0.073 0.033 (methylamino)propan-2- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1307 (R)-8-hydroxy-6-methyl-9-(4-(1- 0.042 0.085 0.057 0.15 0.073 (methylamino)propan-2- yl)phenyl)thieno [2,3-c]quinolin- 4(5H)-one hydrobromide 1309 9-(4-(1-aminobutan-2-yl)phenyl)-8- 0.094 0.066 0.065 0.21 — hydroxythieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1310 (S)-9-(4-(1-aminopropan-2-yl)-3- 0.4 0.8 0.37 0.89 — fluorophenyl)-8-methoxy-6-methyl- thieno[2,3-c]quinolin-4(5H)- one hydrochloride 1311 (R)-9-(4-(1-(dimethylamino)propan-2- 0.037 0.07 0.045 0.11 — yl)-3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin-4(5H)- one hydrochloride 1312 9-(4-(1-aminobutan-2-yl)phenyl)-6- 0.058 0.076 0.054 0.23 — chloro-8-hydroxythieno[2,3- c]quinolin-4(5H)-one hydrochloride 1315 (R)-9-(3-fluoro-4-(1-(methyl- 0.024 0.041 0.034 0.1 — amino)propan-2-yl)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1316 (R)-9-(3-fluoro-4-(1-(methyl- 0.083 0.16 0.086 0.23 — amino)propan-2-yl)phenyl)-8-methoxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1317 (R)-9-(4-(1-aminopropan-2-yl)-3- 0.036 0.072 0.042 0.1 — fluorophenyl)-8-methoxy-6-methyl- thieno[2,3-c]quinolin-4(5H)- one hydrochloride 1318 (R)-9-(4-(1-aminopropan-2-yl)-3- 0.0084 0.015 0.015 0.063 — fluorophenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)- one hydrochloride 1319 (R)-9-(4-(1-aminopropan-2-yl)-3- — 0.016 0.014 0.054 0.014 fluorophenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)- one hydrobromide 1321 9-(4-(1-(aminomethyl)cyclo- 1 2.2 0.8 2 — butyl)phenyl)-6-chloro-8-methoxy- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1324 (R)-9-(4-(1-(dimethylamino)propan- 0.03 0.066 0.024 0.069 — 2-yl)phenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1330 9-(4-(2-aminopropan-2-yl)phenyl)-8- 0.19 0.43 0.18 0.76 — hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1340 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.17 0.25 0.19 0.65 — 8-hydroxy-2,6-dimethylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1341 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.86 0.98 0.57 0.88 — 8-methoxy-2,6-dimethylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1347 (R)-6-chloro-9-(4-(1-(dimethyl- 0.11 0.26 0.1 0.26 — amino)propan-2-yl)phenyl)-8- hydroxythieno [2,3-c]quinolin- 4(5H)-one hydrochloride 1352 (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8- 0.071 0.099 0.055 0.34 — hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1353 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.079 0.087 0.045 0.11 — 2-chloro-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1354 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- 0.29 0.53 0.15 0.23 — 2-chloro-8-methoxy-6- methylthieno[2,3-c]quinolin-4(5H)- one hydrochloride 1364 8-hydroxy-6-methyl-9-(4-(2-(methyl- 0.26 0.3 0.27 0.66 — amino)ethyl)phenyl)thieno[2,3- c]quinolin-4(5H)-one hydrochloride 1372 9-(4-(1-((dimethyl- — 0.084 0.035 0.1 0.075 amino)methyl)cyclobutyl)phenyl)-8- hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1375 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- — 0.42 0.16 0.37 0.35 2-fluoro-8-methoxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1379 (R)-9-(4-(1-(ethyl(methyl)amino)propan- — 0.28 0.11 0.31 0.22 2-yl)phenyl)-8-hydroxy-6-methyl- thieno[2,3-c]quinolin-4(5H)- one hydrochloride 1380 (R)-8-hydroxy-6-methyl-9-(4-(1- — 0.24 0.096 0.37 0.19 (methylamino)butan-2- yl)phenyl)thieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1383 (R)-9-(4-(1-aminopropan-2-yl)phenyl)- — 0.057 0.029 0.1 0.048 2-fluoro-8-hydroxy-6-methylthieno[2,3- c]quinolin-4(5H)-one hydrochloride 1391 9-(4-(1-(aminomethyl)cyclo- — 1.2 0.67 1.4 0.99 propyl)phenyl)-6-bromo-8-methoxy- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1399 (S)-9-(4-(1-(dimethylamino)propan-2- — 0.45 0.18 0.47 0.3 yl)-3-fluorophenyl)-8-hydroxy-6- methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1400 9-(4-((2-amino- — 1.4 0.9 2.8 1.1 ethyl)(methyl)amino)phenyl)-8-hydroxy- 6-methylthieno[2,3-c]quinolin- 4(5H)-one hydrochloride 1401 9-(4-(1-(aminomethyl)cyclo- — 0.4 0.3 1.2 0.34 propyl)phenyl)-6-bromo-8-hydroxy- thieno[2,3-c]quinolin-4(5H)-one hydrochloride 1419 2-(4-(8-hydroxy-6-methyl-4-oxo-4,5- — — 0.72 6.4 0.28 dihydrothieno[2,3-c]quinolin-9- yl)phenyl)propane-1-sulfonamide “>100” in the table means over 100 micro M.

INDUSTRIAL APPLICABILITY

The present invention provides a novel Tricyclic compound having PBK inhibitory effect. The compounds of the present invention may be used for pharmaceutical composition for inhibiting PBK. Such pharmaceutical compositions are suitable for treating or preventing cancer. 

The invention claimed is:
 1. A compound represented by general formula I:

or a pharmaceutically acceptable salt thereof, wherein R¹, R², and R³ are each independently a group selected from the group consisting of: hydrogen, hydroxyl, halogen, cyano, nitro, amino, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₁-C₆ alkoxy, C₆-C₁₀ aryl, indanyl, heteroaryl, 3- to 8-membered heterocycloalkyl, —OSO₂CH₃, —OSO₂CF₃, —CONH₂, —OCONR¹⁰¹R¹⁰², wherein R¹⁰¹ and R¹⁰² each independently is hydrogen, C₁-C₆ alkyl, or R¹⁰¹ and R¹⁰² taken together form morpholinyl, —OCOR¹⁰³, wherein R¹⁰³ represents C₁-C₆ alkyl, and —OCOOR¹⁰⁴, wherein R¹⁰⁴ represents C₁-C₆ alkyl, wherein R¹, R², and R³ are optionally substituted with a substituent independently selected from the group consisting of substituent A; R⁴ is selected from the group consisting of hydroxyl, halogen, amino, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₁-C₆ alkoxy, C₆-C₁₀ aryl, indanyl, heteroaryl, and 3- to 8-membered heterocycloalkyl, and R⁴ is optionally substituted with substituent A; wherein substituent A is independently selected from the group consisting of: hydroxyl; oxo (═O); cyano; halogen; C₁-C₆ alkyl optionally substituted with substituent B; C₃-C₁₀ cycloalkyl optionally substituted with cyano or C₁-C₆ alkyl substituted with —NR³¹R³², wherein R³¹ and R³² each independently represent hydrogen or C₁-C₆ alkyl; —NR²¹R²², wherein R²¹ and R²² each independently represent hydrogen; C₁-C₆ alkyl optionally substituted with hydroxyl, amino, di(C₁-C₆ alkyl)amino, —SO₂(C₁-C₆ alkyl), 3- to 8-membered heterocycloalkyl, or cyano; or a 3- to 8-membered heterocycloalkyl optionally substituted with —COOR¹⁰⁵ wherein R¹⁰⁵ represents C₁-C₆ alkyl; C₁-C₆ alkoxy optionally substituted with halogen, 3- to 8-membered heterocycloalkyl optionally substituted with C₁-C₆ alkyl, or —NR³³R³⁴ wherein R³³ and R³⁴ each independently represent hydrogen, C₁-C₆ alkylsulfonyl, or C₁-C₆ alkyl optionally substituted with C₁-C₆ alkylsulfonyl or di(C₁-C₆ alkyl)amino; —SO₂NR²³R²⁴, wherein R²³ and R²⁴ each independently represent hydrogen; C₁-C₆ alkyl optionally substituted with hydroxyl, C₁-C₆ alkoxy, halogen, C₃-C₁₀ cycloalkyl, heteroaryl, or —NR³⁵R³⁶ wherein R³⁵ and R³⁶ each independently represent hydrogen or C₁-C₆ alkyl; C₃-C₁₀ cycloalkyl optionally substituted with C₁-C₆ hydroxyalkyl; 3- to 8-membered heterocycloalkyl; or R²³ and R²⁴ taken together form 3- to 8-membered heterocycloalkyl optionally substituted with amino or halogen; C₁-C₆ alkylsulfonyl optionally substituted with hydroxyl; —NHSO₂(C₁-C₆ alkyl), wherein the carbon atoms are optionally substituted with —NR³⁷R³⁸ wherein R³⁷ and R³⁸ each independently represent hydrogen or C₁-C₆ alkyl; 3- to 8-membered heterocycloalkyl optionally substituted with —NR³⁹R⁴⁰, wherein R³⁹ and R⁴⁰ each independently represent hydrogen, C₁-C₆ alkyl, or C₁-C₆ alkylsulfonyl; C₁-C₆ alkyl optionally substituted with —NR⁴¹R⁴², wherein R⁴¹ and R⁴² each independently represent hydrogen or C₁-C₆ alkyl; hydroxyl; or C₁-C₆ alkylsulfonyl; aryl optionally substituted with C₁-C₆ alkyl optionally substituted with cyano or amino; heteroaryl; —COOR¹¹, wherein R¹¹ represents hydrogen or C₁-C₆ alkyl; and —COR¹², wherein R¹² represents C₁-C₆ alkyl; C₃-C₁₀ cycloalkyl; cyanomethyl; aminomethyl; —NR²⁵R²⁶ wherein R²⁵ and R²⁶ each independently represent hydrogen or C₁-C₆ alkyl optionally substituted with hydroxyl or —NR⁴³R⁴⁴, wherein R⁴³ and R⁴⁴ each independently represent hydrogen or C₁-C₆ alkyl; or 3- to 8-membered heterocycloalkyl optionally substituted with C₁-C₆ alkyl; wherein substituent B is independently selected from the group consisting of: halogen; hydroxyl; C₁-C₆ alkoxy; cyano; cycloalkyl; C₆-C₁₀ aryl optionally substituted with cyano; heteroaryl; 3- to 8-membered heterocycloalkyl optionally substituted with C₁-C₆ alkyl, hydroxyl, amino, C₁-C₆ aminoalkyl, or C₁-C₆ alkyl substituted with C₂-C₇ alkyloxycarbonylamino; —NR⁵¹R⁵², wherein R⁵¹ and R⁵² each independently represent hydrogen; C₁-C₆ alkyl optionally substituted with C₁-C₆ alkylsulfonyl or 3- to 8-membered heterocycloalkyl optionally substituted with —COOR⁵³ wherein R⁵³ represents hydrogen or C₁-C₆ alkyl; 3- to 8-membered heterocycloalkyl; C₁-C₆ alkylsulfonyl; C₃-C₁₀ cycloalkyl; —COR⁵⁵ wherein R⁵⁵ represents C₁-C₆ alkyl; —COOR⁵⁶ wherein R⁵⁶ represents C₁-C₆ alkyl; or —CONR⁵⁷R⁵⁸ wherein R⁵⁷ and R⁵⁸ each independently represent hydrogen or C₁-C₆ alkyl; —COOR⁵⁴, wherein R⁵⁴ represents hydrogen or C₁-C₆ alkyl; —CONH₂; —SO₂NR¹⁰⁶R¹⁰⁷, wherein R¹⁰⁶ and R¹⁰⁷ each independently represent hydrogen, C₁-C₆ alkyl, or C₃-C₁₀ cycloalkyl; C₁-C₆ alkylsulfinyl; and C₁-C₆ alkylsulfonyl; wherein R⁵ is hydrogen or C₁-C₆ alkyl; and wherein

 is the structure: —S—CR⁷═CR⁶—, wherein R⁶ is selected from the group consisting of: hydrogen, hydroxyl, C₁-C₆ alkyl, C₆-C₁₀ aryl optionally substituted with hydroxyl, and 3- to 8-membered heterocycloalkyl optionally substituted with —NR⁶¹R⁶², wherein R⁶¹ and R⁶² each independently represent hydrogen or C₁-C₆ alkyl; wherein R⁷ is selected from the group consisting of: hydrogen; halogen; C₁-C₆ alkyl optionally substituted with hydroxyl, —NR⁷¹R⁷² wherein R⁷¹ and R⁷² each independently represent hydrogen; C₁-C₆ alkyl optionally substituted with dimethylamino; C₃-C₁₀ cycloalkyl optionally substituted with amino or 3- to 8-membered heterocycloalkyl; or 3- to 8-membered heterocycloalkyl optionally substituted with C₁-C₆ aminoalkyl; C₆-C₁₀ aryl optionally substituted with hydroxyl; C₆-C₁₀ arylsulfonyl; and —COR⁷³, wherein R⁷³ represents 3- to 8-membered heterocycloalkyl optionally substituted with amino; or —NR⁷⁴R⁷⁵ wherein R⁷⁴ and R⁷⁵ each independently represent hydrogen, 3- to 8-membered heterocycloalkyl, or C₃-C₁₀ cycloalkyl optionally substituted with amino.
 2. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R¹ is hydrogen, cyano, C₁-C₆ alkyl optionally substituted with hydroxyl or halogen, C₃-C₁₀ cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, or halogen.
 3. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R² is hydrogen, hydroxyl, halogen, C₁-C₆ alkoxy, or C₆-C₁₀ aryl optionally substituted with hydroxyl.
 4. The compound of claim 1, or a pharmaceutically acceptable salt, wherein R² is hydrogen, hydroxyl, halogen, C₁-C₆ alkoxy, or dihydroxyphenyl.
 5. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R³ is selected from the group consisting of: hydrogen; hydroxyl; C₁-C₆ alkyl optionally substituted with hydroxyl, halogen, or hydroxyethylamino; halogen; C₁-C₆ alkoxy optionally substituted with dimethylamino or morpholinyl; C₁-C₆ alkylphenyl, wherein the aliphatic carbons are optionally substituted with —NR⁵¹R⁵²; cyano; nitro; amino; 3- to 8-membered heterocycloalkyl optionally substituted with amino; heteroaryl; —OSO₂CH₃; —OSO₂CF₃; —OCOR¹⁰³, wherein R¹⁰³ represents C₁-C₆ alkyl; —OCOOR¹⁰⁴ wherein R¹⁰⁴ represents C₁-C₆ alkyl; —OCONR¹⁰¹R¹⁰² wherein R¹⁰¹ and R¹⁰² each independently represent hydrogen or C₁-C₆ alkyl, or R¹⁰¹ and R¹⁰² taken together form morpholinyl; and —CONH₂.
 6. The compound of claim 5, or a pharmaceutically acceptable salt thereof, wherein when R³ is a 3- to 8-membered heterocycloalkyl, the 3- to 8-membered heterocycloalkyl is selected from the group consisting of piperidyl, pyrrolidinyl, morpholinyl, or piperazinyl and optionally substituted with amino; and when R³ is heteroaryl, the heteroaryl is pyridyl.
 7. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein when R⁴ is heteroaryl, the heteroaryl is selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl); and wherein the 3- to 8-membered heterocycloalkyl is selected from the group consisting of aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, azepanyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl; wherein each of the groups of R⁴ is optionally substituted with substituent A-1; wherein substituent A-1 is selected from the group consisting of: hydroxyl; oxo; cyano; halogen; C₁-C₆ alkyl optionally substituted with a substituent selected from the group consisting of substituent B-1; C₃-C₁₀ cycloalkyl optionally substituted with cyano, or C₁-C₆ alkyl substituted with —NR³¹R³²; —NR^(21A)R^(22A), wherein R^(21A) and R^(22A) each independently represent hydrogen; C₁-C₆ alkyl optionally substituted with amino, di(C₁-C₆ alkyl)amino, —SO₂ (C₁-C₆ alkyl), piperidyl, or cyano; or piperidyl optionally substituted with —COOR¹⁰⁵; C₁-C₆ alkoxy optionally substituted with halogen; a 3- to 8-membered heterocycloalkyl selected from piperidyl and piperazinyl, either of which is optionally substituted with C₁-C₆ alkyl; or —NR³³R³⁴; —SO²NR^(23A)R^(24A), wherein R^(23A) and R^(24A) each independently represent hydrogen, C₁-C₆ alkyl optionally substituted with hydroxyl, C₁-C₆ alkoxy, halogen, C₃-C₁₀ cycloalkyl, pyrazolyl, imidazolyl, or —NR³⁵R³⁶; C₃-C₁₀ cycloalkyl optionally substituted with C₁-C₆ hydroxyalkyl; azetidinyl; pyrrolidinyl, or R^(23A) and R^(24A) taken together form pyrrolidinyl optionally substituted with amino or halogen; C₁-C₆ alkylsulfonyl optionally substituted with hydroxyl; —NHSO₂(C₁-C₆ alkyl), wherein the carbon atoms are optionally substituted with —NR³⁷R³⁸; 3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, piperidyl, piperazinyl, and tetrahydropyridyl any of which is optionally substituted with —NR³⁹R⁴⁰; C₁-C₆ alkyl optionally substituted with —NR⁴¹R⁴²; hydroxyl; or C₁-C₆ alkylsulfonyl; 1H-tetrazolyl; aryl optionally substituted with C₁-C₆ alkyl, wherein C₁-C₆ is the aliphatic carbons are optionally substituted with cyano or amino; —COOR¹¹; and —COR^(12A), wherein R^(12A) represents piperazinyl optionally substituted with C₁-C₆ alkyl; C₃-C₁₀ cycloalkyl; cyanomethyl; aminomethyl; —NR²⁵R²⁶ wherein R²⁵ and R²⁶ each independently represent hydrogen or C₁-C₆ alkyl optionally substituted with hydroxyl or —NR⁴³R⁴⁴; or C₁-C₆ alkylsulfonyl; wherein substituent B-1 is selected from the group consisting of: halogen; hydroxyl; C₁-C₆ alkoxy; cyano; cycloalkyl; phenyl optionally substituted with cyano; heteroaryl selected from the group consisting of imidazolyl, pyrazolyl, and thiazolyl; 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and oxetanyl any of which are optionally substituted with hydroxyl, amino, C₁-C₆ aminoalkyl, or C₁-C₆ alkyl optionally substituted with C₂-C₇ alkyloxycarbonylamino; —NR^(51A)R^(52A), wherein R^(51A) and R^(52A) each independently represent hydrogen; C₁-C₆ alkyl optionally substituted with C₁-C₆ alkylsulfonyl or piperidyl optionally substituted with —COOR⁵³; piperidyl; C₁-C₆ alkylsulfonyl; C₃-C₁₀ cycloalkyl; —COR⁵⁵, —COOR⁵⁶, or —CONR⁵⁷R⁵⁸; —COOR⁵⁴; —CONH₂; —SO₂NR¹⁰⁶R¹⁰⁷; C₁-C₆ alkylsulfinyl; and C₁-C₆ alkylysulfonyl.
 8. The compound of claim 7, or a pharmaceutically acceptable salt thereof, wherein R⁴ is a group selected from group (p): wherein group (p) is independently selected from the group consisting of: hydroxyl, halogen, amino optionally substituted with a substituent selected from the group consisting of substituent (g), C₁-C₆ alkyl optionally substituted with a substituent selected from the group consisting of substituent (a), C₂-C₆ alkenyl optionally substituted with a substituent selected from the group consisting of substituent (b), C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₁-C₆ alkoxy, C₆-C₁₀ aryl optionally substituted with a substituent selected from the group consisting of substituent (c), indanyl optionally substituted with a substituent selected from the group consisting of substituent (d), heteroaryl selected from the group consisting of pyridyl, 1H-indazolyl, 1H-tetrazolyl, [1,2,4]triazolo[1,5-a]pyridyl, benzoimidazolyl, 2,3-dihydrobenzooxazolyl, pyrazolyl, pyrrolo[2,3-b]pyridyl, pyrimidinyl, indolinyl, furyl, thienyl, and tetrahydroisoquinolyl any of which is optionally substituted with a substituent selected from the group consisting of substituent (e); and 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and 1,2,3,6-tetrahydropyridyl any of which is optionally substituted with a substituent selected from the group consisting of substituent (f); wherein substituent (a) is selected from the group consisting of: NR^(21A)R^(22A), wherein R^(21A) and R^(22A) each independently represent hydrogen; C₁-C₆ alkyl optionally substituted with piperidyl; or piperidyl optionally substituted with —COOR¹⁰⁵; 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl and piperidyl either of which is optionally substituted with C₁-C₆ alkyl optionally substituted with —NR⁴¹R⁴² or —NR³⁹R⁴⁰ wherein R³⁹ and R⁴⁰ each independently represent hydrogen or C₁-C₆ alkyl; and —NHSO₂(C₁-C₆ alkyl); wherein substituent (b) is selected from the group consisting of: —COOR¹¹; —NR^(21a)R^(22a), wherein R^(21a) and R^(22a) each independently represent hydrogen, or C₁-C₆ alkyl optionally substituted with di(C₁-C₆ alkyl)amino or C₁-C₆ alkylsulfonyl; 3- to 8-membered heterocycloalkyl selected from the group consisting of azetidinyl, pyrrolidinyl, and piperidyl any of which are optionally substituted with —NR³⁹R⁴⁰, C₁-C₆ alkyl optionally substituted with —NR⁴¹R⁴², hydroxyl, or C₁-C₆ alkylsulfonyl; cyano; and C₁-C₆ alkoxy; wherein substituent (c) is selected from the group consisting of: hydroxyl; cyano; halogen; C₁-C₆ alkyl optionally substituted with a substituent selected from the group consisting of substituent B-c below; C₃-C₁₀ cycloalkyl optionally substituted with cyano, or C₁-C₆ alkyl substituted with —NR³¹R³²; —NR^(21c)R^(22c), wherein R^(21c) and R^(22c) each independently represent hydrogen or C₁-C₆ alkyl optionally substituted with amino or cyano; C₁-C₆ alkoxy optionally substituted with halogen, 3- to 8-membered heterocycloalkyl selected from the group consisting of piperidyl and piperazinyl either of which are optionally substituted with C₁-C₆ alkyl, or —NR³³R³⁴; —SO₂NR^(23c)R^(24c), wherein R^(23c) and R^(24c) each independently represent hydrogen, C₁-C₆ alkyl optionally substituted with hydroxyl, C₁-C₆ alkoxy, halogen, C₃-C₁₀ cycloalkyl, pyrazolyl, imidazolyl, or —NR³⁵R³⁶; C₃-C₁₀cycloalkyl optionally substituted with C₁-C₆ hydroxyalkyl; azetidinyl, pyrrolidinyl, or wherein R^(23c) and R^(24c) taken together form pyrrolidinyl which is optionally substituted with amino or halogen; C₁-C₆ alkylsulfonyl optionally substituted with hydroxyl; —NHSO₂(C₁-C₆ alkyl), wherein the carbon atoms are optionally substituted with —NR³⁷R³⁸; piperazinyl optionally substituted with C₁-C₆ alkyl or C₁-C₆ alkylsulfonyl; piperidyl optionally substituted with hydroxyl; 1H-tetrazolyl; 1,2,3,6-tetrahydropyridyl; and —COR^(12c), wherein R^(12c) represents piperazinyl which is optionally substituted with C₁-C₆ alkyl, C₃-C₁₀ cycloalkyl, cyanomethyl, aminomethyl, —NR²⁵R²⁶, or C₁-C₆ alkyl; and wherein substituent B-c is selected from the group consisting of: halogen; hydroxyl; methoxy; cyano; C₃-C₁₀ cycloalkyl; 3- to 8-membered heterocycloalkyl selected from the group consisting of pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, and oxetanyl, any of which is optionally substituted with C₁-C₆ alkyl, hydroxyl, amino, C₁-C₆ aminoalkyl, or C₁-C₆ alkyl substituted with C₂-C₇ alkyloxycarbonylamino; —NR^(51c)R^(52c), wherein R^(51c) and R^(52c) each independently represent hydrogen; C₁-C₆ alkyl optionally substituted with C₁-C₆ alkylsulfonyl, or piperidyl optionally substituted with —COOR⁵³; piperidyl; C₁-C₆alkylsulfonyl; C₃-C₁₀ cycloalkyl; —COR⁵⁵; or —CONR⁵⁷R⁵⁸; heteroaryl selected from the group consisting of imidazolyl, pyrazolyl, and thiazolyl; —CONH₂; —SO₂NR¹⁰⁶R¹⁰⁷; C₁-C₆ alkylsufinyl; and C₁-C₆ alkylsulfonyl; wherein substituent (d) is selected from the group consisting of: —NR^(21d)R^(22d), wherein R^(21d) and R^(22d) each independently represent hydrogen or C₁-C₆ alkyl; wherein substituent (e) is selected from the group consisting of: hydroxyl; oxo; cyano; C₃-C₁₀ cycloalkyl optionally substituted with cyano; —NR^(21e)R^(22e), wherein R^(21e) and R^(22e) each independently represent hydrogen or C₁-C₆ alkyl optionally substituted with amino; piperidyl; C₁-C₆ alkoxy optionally substituted with —NR³³R³⁴; C₁-C₆ alkyl optionally substituted with cyano; —NR^(51e)R^(52e), wherein R^(51e) and R^(52e) each independently represent hydrogen, C₁-C₆ alkyl, or —COOR⁵⁶; morpholinyl; or cyanophenyl; —CONH₂; wherein substituent (f) is selected from the group consisting of: C₁-C₆ alkyl optionally substituted with —NR^(51f)R^(52f), wherein R^(51f) and R^(52f) each independently represent hydrogen, C₁-C₆ alkyl, or —COOR⁵⁶; and C₁-C₆ alkylsulfonyl; wherein substituent (g) is aryl optionally substituted with C₁-C₆ alkyl having the aliphatic carbons optionally substituted with cyano or amino.
 9. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R⁶ is hydrogen; hydroxyl; C₁-C₆ alkyl; phenyl optionally substituted with 1 to 3 hydroxyls; piperidyl optionally substituted with amino; or piperazinyl.
 10. The compound of claim 9, or a pharmaceutically acceptable salt thereof, wherein R⁷ is hydrogen; C₁-C₆ alkyl optionally substituted with hydroxyl or piperidyl; or halogen.
 11. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R⁷ is hydrogen; C₁-C₆ alkyl optionally substituted with hydroxyl; —NR^(71A)R^(72A) wherein R^(71A) and R^(72A) each independently represent hydrogen, C₁-C₆ alkyl optionally substituted with dimethylamino, C₃-C₁₀ cycloalkyl optionally substituted with amino, or piperidyl; or 3- to 8-membered heterocycloalkyl selected from the group consisting of piperidyl and morpholinyl either of which is optionally substituted with C₁-C₆ aminoalkyl; phenyl optionally substituted with 1 to 2 hydroxyls; phenylsulfonyl; or —COR^(73A), wherein R^(73A) represents piperidyl optionally substituted with amino, or —NR^(74A)R^(75A), wherein R^(74A) and R^(75A) each independently represent hydrogen, piperidyl, or C₃-C₁₀ cycloalkyl optionally substituted with amino.
 12. A compound selected from the group consisting of: (6): 7,9-dimethoxythieno[2,3-c]quinolin-4(5H)-one; (7): 7,9-dihydroxythieno[2,3-c]quinolin-4(5H)-one; (8): 7,8,9-trimethoxythieno[2,3-c]quinolin-4(5H)-one; (10): 7,8,9-trihydroxythieno[2,3-c]quinolin-4(5H)-one; (11): 9-(3-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (42): 9-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (43): 9-(3,4-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (47): 9-(3,5-dihydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (48): 8-hydroxy-9-(3-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; (49): 8-hydroxy-9-(4-hydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; (50): 9-(3,4-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (52): 5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)picolinonitrile; (53): 9-(6-aminopyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (54): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; (55): 9-(3-fluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (58): 9-(3,4-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (59): 9-(4-fluoro-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (60): 8-hydroxy-9-(3-hydroxy-5-(trifluoromethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (61): 8-hydroxy-9-(1H-indazol-6-yl)thieno[2,3-c]quinolin-4(5H)-one; (62): 8-hydroxy-9-(3,4,5-trihydroxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; (63): 9-(4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (64): 9-(4-(1H-tetrazol-5-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (65): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (66): 9-(3-chloro-4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (67): 9-(4-chloro-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (68): 9-(3,4-dichlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (69): 9-(4-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (70): 8-hydroxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one; (71): 9-(4-(difluoromethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (72): 9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (73): 9-(4-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (74): 9-(3-aminophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (75): 3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (76): 8-hydroxy-9-(3,4,5-trifluorophenyl)thieno[2,3-c]quinolin-4(5H)-one; (77): N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; (78): 8-methoxy-9-phenylthieno[2,3-c]quinolin-4(5H)-one; (79): 8-hydroxy-9-(naphthalen-2-yl)thieno[2,3-c]quinolin-4(5H)-one; (80): 8-hydroxy-9-(4-(hydroxymethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (81): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; (82): 8-hydroxy-9-(4-(methylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (83): 8-hydroxy-9-(pyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (84): 8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (85): 8-hydroxy-9-(4-hydroxy-3-methoxyphenyl)thieno[2,3-c]quinolin-4(5H)-one; (86): 9-(3-fluoro-4-(morpholinomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (87): 9-(3-(aminomethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (88): 9-(4-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (89): 9-(3-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (90): 9-(3-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one; (91): 9-cyclohexenyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (92): 9-(3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (93): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (94): 9-(3-(aminomethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (95): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one; (96): 9-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (97): 9-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (98): 8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (99): 9-cyclohexenyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (100): 8-methoxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (101): 9-(4-(aminomethyl)phenyl)-8-hydroxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one; (102): 9-(1H-benzo[d]imidazol-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (103): 9-(4-(difluoromethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (104): 9-(4-(aminomethyl)phenyl)-8-methoxy-2-(morpholinomethyl)thieno[2,3-c]quinolin-4(5H)-one; (105): 8-hydroxy-9-(4-(2-(piperidin-1-yl)ethylamino)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (106): 8-hydroxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (109): 5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzo[d]oxazol-2(3H)-one; (110): tert-butyl 4-(2-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylamino)ethyl)piperidine-1-carboxylate; (111): 8-methoxy-9-(4-(piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (112): 8-hydroxy-9-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (113): 8-hydroxy-9-(4-((piperidin-3-ylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (114): N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; (115): 9-(4-(3-(dimethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (116): 8-methoxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (117): 8-hydroxy-9-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (120): N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; (122): (E)-butyl 3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)acrylate; (123): 8-methoxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; (124): 8-hydroxy-9-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; (125): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide; (126): N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; (127): N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; (128): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)acetamide; (130): 8-hydroxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (131): 8-methoxy-9-(4-(4-methylpiperazine-1-carbonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (132): 8-hydroxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (133): 8-methoxy-9-(4-((4-methylpiperazin-1-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (134): (E)-9-(3-(diethylamino)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (135): (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (136): (E)-9-(3-(2-(diethylamino)ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (138): 9-(2-(dimethylamino)pyrimidin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (139): tert-butyl (1-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)piperidin-4-yl)methylcarbamate; (140): 8-hydroxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (141): 8-methoxy-9-(4-(4-methylpiperazin-1-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (142): 8-methoxy-9-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (143): (E)-9-(3-(diethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (144): 9-(3-(4-(aminomethyl)piperidin-1-yl)propyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (145): 9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (146): 9-(4-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (147): 9-(4-(3-(2-(diethylamino)ethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (148): (E)-9-(3-(4-(aminomethyl)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4 (5H)-one; (149): 9-(4-(3-(dimethylamino)propoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (150): 8-hydroxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (151): 9-(4-(2-(ethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (152): (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (153): 9-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (154): 9-(4-(2-(ethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (155): 9-(4-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (156): 9-(4-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (157): 9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (158): 9-(4-(2-(dimethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (159): 8-methoxy-9-(4-(2-(piperidin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (160): 8-methoxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (161): 9-(3-(2-(diethylamino)ethoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (162): 9-(3-(3-(diethylamino)propoxy)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (163): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (164): 9-(4-((dimethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (165): 9-(4-((dimethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (166): 9-(3-(2-(diethylamino)ethoxy)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (167): 8-hydroxy-9-(3-(2-(4-methylpiperazin-1-yl)ethoxy)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (168): N-ethyl-N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylmethoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenoxy)ethyl)methanesulfonamide; (169): 9-(4-(2-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (170): 2-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; (171): 2-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; (172): 9-(1-(2-(dimethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (173): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; (174): 9-(1-(2-(diethylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (175): 9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (176): 9-(4-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (177): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; (178): N-(methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; (179): N-(2-aminoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (183): 9-(4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (184): 9-(4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (185): 9-(3-(2-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (186): 9-(3-(2-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (187): 8-hydroxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (188): 8-methoxy-9-(4-((methylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (189): 9-(4-amino-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (190): 3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile; (191): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (192): 9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (193): N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide; (194): 8-hydroxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (195): 9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (196): 9-(4-(1-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (197): N-(2-aminoethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (198): N-(2-(dimethylamino)ethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (199): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(pyrrolidin-3-yl)benzenesulfonamide; (200): N-(azetidin-3-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (201): 9-(4-(2-(diethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (202): 2-amino-N-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; (203): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile; (204): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzonitrile; (205): (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (206): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (207): 8-methoxy-9-(5-methoxypyridin-3-yl)thieno[2,3-c]quinolin-4(5H)-one; (209): 9-(4-(3-aminopyrrolidin-1-ylsulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (210): N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (211): 9-(4-((diisopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (212): N-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)methanesulfonamide; (213): 9-(4-((isopropylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (214): 2-(dimethylamino)-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; (215): 2-amino-N-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; (216): 8-methoxy-9-(4-(1-(pyrrolidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (217): 9-(4-amino-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (218): N-(2-methoxy-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; (219): 9-(3,5-difluoro-4-hydroxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (220): N-(2-hydroxy-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; (221): 9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (222): 9-(4-(2-(dimethylamino)ethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (223): 9-(3,5-difluoro-4-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (224): 6-fluoro-8-methoxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (225): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (226): 9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (227): (E)-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (228): (E)-8-hydroxy-9-(3-(3-hydroxypyrrolidin-1-yl)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one; (229): 8-hydroxy-9-(4-((isopropylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (230): (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (231): (E)-8-methoxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one; (232): (S)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (233): (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (235): 9-(4-((4-(aminomethyl)piperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (236): 8-methoxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (237): 9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (238): (E)-9-(3-(3-aminoazetidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (239): (E)-9-(3-(ethylamino)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (240): 9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (241): 9-(4-((3-aminopyrrolidin-1-yl)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (242): 9-(4-((3-aminopiperidin-1-yl)methyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (243): 8-hydroxy-9-(4-(1-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (244): (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (245): (E)-9-(3-(3-aminopyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (246): (E)-9-(3-(3-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (247): (E)-8-hydroxy-9-(3-(2-(methylsulfonyl)ethylamino)prop-1-enyl)thieno[2,3-c]quinolin-4(5H)-one; (248): 8-methoxy-9-(4-(2-(2-(methylsulfonyl)ethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (249): 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; (250): (E)-N-(1-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)allyl)azetidin-3-yl)methanesulfonamide; (251): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide; (252): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide; (253): tert-butyl (5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)furan-2-yl)methylcarbamate; (254): N-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide; (255): N-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylphenyl)methanesulfonamide; (256): 9-(4-(aminomethyl)phenyl)-6-fluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (257): 9-(4-(aminomethyl)phenyl)-6-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (258): 6-fluoro-8-hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (259): 9-(4-((diethylamino)methyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (260): 8-methoxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (261): 2-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)acetonitrile; (262): 8-hydroxy-9-(4-(1-(piperidin-1-yl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (263): (E)-9-(3-(3-(dimethylamino)piperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (264): (E)-9-(3-(3-(dimethylamino)pyrrolidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (265): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (266): 9-(5-(aminomethyl)thiophen-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (267): 9-(4-((ethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (268): (E)-9-(3-(4-aminopiperidin-1-yl)prop-1-enyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (269): 9-(4-((ethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (270): 9-(4-(aminomethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (271): 9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (272): (R)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (273): 9-(4-(3-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (274): (R)-9-(4-(1-aminoethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (275): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (276): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (277): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (278): 9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (279): 9-(3-fluoro-4-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (280): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide; (281): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2,2,2-trifluoroethyl)benzenesulfonamide; (282): N-(2-(dimethylamino)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (283): 8-hydroxy-9-(4-((2-(methylsulfonyl)ethylamino)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (284): 9-(3-(3-(dimethylamino)pyrrolidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (285): 9-(1-(2-aminoethyl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (286): 9-(3-chloro-4-((diethylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (287): 4-(7-fluoro-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; (288): 9-(3-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (289): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide; (290): 3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; (291): 9-(4-acetylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (292): 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; (293): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzamide; (294): 1,1-diethyl-3-(hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)urea; (295): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzamide; (296): 9-(4-acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (297): N-(2-bromoethyl)-2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (298): 9-(3-(3-(dimethylamino)piperidin-1-yl)propyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (299): N-(2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl)methanesulfonamide; (300): 9-(3-fluoro-4-(2-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate; (301): (R)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide; (302): (R)-9-(4-(1-(methylsulfonamido)ethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate; (303): 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (304): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N,N-dimethylbenzenesulfonamide; (305): 9-(4-(2-(dimethylamino)ethyl)phenyl)-7-fluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (306): N-(2-bromoethyl)-4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (307): 4-(7-fluoro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; (308): 9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (309): N-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzyl)-N-methylmethanesulfonamide; (310): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide; (311): (E)-3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-methylacrylonitrile; (312): N-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyemethanesulfonamide; (313): 8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (314): 9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (315): 9-(4-(1-(cyclopentylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (316): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; (317): 9-(5-(aminomethyl)furan-2-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (318): 9-(3-chloro-4-((methylamino)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (319): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (320): N-(3-hydroxypropyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (321): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; (322): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3-hydroxypropyl)benzenesulfonamide; (323): N-(3-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (324): 2-fluoro-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-methoxyethyl)benzenesulfonamide; (325): 9-(3-chloro-4-((methylamino)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (326): 9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; (327): 9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (328): 9-(4-(aminomethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (329): 9-(4-(aminomethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (330): 9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl trifluoromethanesulfonate; (331): 9-(4-(2-(dimethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (332): N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (333): N-(2-fluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (334): 9-(4-(2-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (335): (S)-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (336): 9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (337): 9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (338): 9-(4-(1-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (339): 9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (340): 9-amino-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (341): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (342): 9-(4-(1-(dimethylamino)ethyl)phenyl)-6,7-difluoro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (343): N-cyclopropyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (344): N-cyclopropyl-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (345): 9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (346): 9-(4-(1-(dimethylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (347): (S)—N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)methanesulfonamide; (348): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (349): 9-(4-(1-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (350): N-(1-(hydroxymethyl)cyclopentyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (351): 9-(2-(diethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (352): 9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (353): 8-hydroxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one; (354): 8-methoxy-9-(1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one; (355): 3-(3-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; (356): 9-(4-(1-(diethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (357): 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile; (358): 9-(2-ethyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (359): 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (360): 3-(3-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; (361): 1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)cyclopropanecarbonitrile; (362): 9-(2-amino-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (363): N-isopentyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (364): 9-(2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (365): 9-(4-(1-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (366): 6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (367): 9-(4-(cyclopropanecarbonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (368): 9-(4-(aminomethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carboxamide; (369): 9-(2-aminoethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (370): 8-hydroxy-9-(4-(2-hydroxyethylsulfonyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (371): 9-(4-(2-hydroxyethylsulfonyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (372): 9-(1-ethylindolin-5-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (373): 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (374): 8-hydroxy-9-(2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)thieno[2,3-c]quinolin-4(5H)-one; (375): 9-(4-(1-aminoethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (376): 8-hydroxy-9-(1-methylindolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; (377): 8-hydroxy-9-(indolin-5-yl)thieno[2,3-c]quinolin-4(5H)-one; (378): 9-(indolin-5-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (379): 9-(4-(1-((dimethylamino)methyl)cyclopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (380): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-propylbenzenesulfonamide; (381): N-(cyclopropylmethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (382): N-(3,3-dimethylbutyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (383): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-isopentylbenzenesulfonamide; (384): N-(3,3-dimethylbutyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (385): 9-(4-(1-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (386): 3-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-oxopropanenitrile; (387): (E)-9-(2-ethoxyvinyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (388): N-(1-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethyl)acetamide; (389): 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide; (390): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(1-(hydroxymethyl)cyclopentyl)benzenesulfonamide; (391): N-(2,2-difluoroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1031): 8-methoxy-9-(4-(1-methoxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1032): 9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1033): 8-methoxy-9-(2-((piperidin-3-ylmethyl)amino)ethyl)thieno[2,3-c]quinolin-4(5H)-one; (1034): 9-(2-(4-((dimethylamino)methyl)piperidin-1-yl)ethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1035): tert-butyl 4-((2-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)ethyl)amino)piperidine-1-carboxylate; (1036): 8-methoxy-9-(2-(piperidin-4-ylamino)ethyl)thieno[2,3-c]quinolin-4(5H)-one; (1037): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(3,3,3-trifluoropropyl)benzenesulfonamide; (1039): 9-(4-(1-aminoethyl)phenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1040): 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-6-carbonitrile; (1041): 9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1042): 8-hydroxy-9-(2-(4-((methylamino)methyl)piperidin-1-yl)ethyl)thieno[2,3-c]quinolin-4(5H)-one; (1043): 8-methoxy-9-(2-(4-((methylamino)methyl)piperidin-1-yl)ethyl)thieno[2,3-c]quinolin-4(5H)-one; (1044): 9-(2-(4-((dimethylamino)methyl)piperidin-1-yl)ethyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1045): 9-(4-(1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1046): (R)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1049): 9-(4-(4-hydroxypiperidin-4-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1051): 8-hydroxy-9-(4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1052): (R)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1053): 8-hydroxy-9-(4-(1-hydroxypropyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1054): (R)-8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1055): 8-hydroxy-9-(4-(4-hydroxypiperidin-4-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1056): (S)-8-hydroxy-9-(4-(1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1057): N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1058): 9-(4-(hydroxy(thiazol-2-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1059): 9-(6-(1-aminoethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1060): 9-(4-(4-hydroxybutyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1061): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropanamide; (1062): N-(1-bromopropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1063): 8-hydroxy-9-(4-(hydroxy(thiazol-2-yl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1064): (S)-8-methoxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1065): 9-(6-(1-(diethylamino)ethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1066): 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1067): 9-(6-(1-aminoethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1068): 8-hydroxy-9-(4-(4-hydroxybutyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1069): 9-(4-(3-amino-1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1070): 9-(6-(1-(dimethylamino)ethyl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1071): 9-(6-(1-(dimethylamino)ethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1072): 4-((4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-1H-pyrazol-1-yl)methyl)benzonitrile; (1074): 9-(4-((1H-pyrazol-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1075): 9-(6-(1-aminoethyl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1076): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl dimethylcarbamate; (1077): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl isopropyl carbonate; (1078): 9-(4-((1H-imidazol-1-yl)methyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1079): N-(2-bromopropyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1080): (R)-9-(4-(1-aminoethyl)phenyl)-6,7-dichloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1081): (R)-9-(4-(1-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1082): (S)-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1083): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl diethylcarbamate; (1084): 4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide; (1085): N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide; (1086): 9-(4-((1H-pyrazol-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1087): (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1088): 9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1089): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl morpholine-4-carboxylate; (1091): 8-bromothieno[2,3-c]quinolin-4(5H)-one; (1092): 9-(4-(2-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1093): 9-(4-(2-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1095): 9-(4-(2-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1096): 8-methoxy-9-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (1097): 9-(4-(2-(diethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1098): 9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one; (1099): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl acetate; (1100): 9-(1-(1-(dimethylamino)propan-2-yl)-1H-pyrazol-4-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1101): 9-(4-((1H-imidazol-1-yl)methyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1102): 9-(4-(aminomethyl)phenyl)-8-(2-morpholinoethoxy)thieno[2,3-c]quinolin-4(5H)-one; (1103): 8-hydroxy-9-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)thieno[2,3-c]quinolin-4(5H)-one; (1104): N-(2-(1H-pyrazol-1-yl)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1105): 8-hydroxy-9-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1106): 9-(4-(2-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1107): N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-methylpropyl)methanesulfonamide; (1108): 9-(4-(2-(dimethylamino)propyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1109): 9-(4-(1-aminoethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1110): 9-(1-(1-(dimethylamino)propan-2-yl)-1H-pyrazol-4-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1111): 9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1112): 9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1113): 8-methoxy-9-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1114): N-(2-bromoethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide; (1115): N-(2-(1H-imidazol-1-yl)ethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1116): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1117): 3-(4-(8-(2-(dimethylamino)ethoxy)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; (1118): (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1119): N-(2-chloroethyl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-methylbenzenesulfonamide; (1120): (S)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1121): (S)-9-(4-(1-aminopropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1122): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1123): (R)-9-(4-(1-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1124): 9-(4-(1-aminoethyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; (1125): 9-(4-(1-aminoethyl)phenyl)-8-(hydroxymethyl)thieno[2,3-c]quinolin-4(5H)-one; (1126): (R)-6-chloro-9-(4-(1-(dimethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1127): (S)-9-(4-(1-(ethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1128): (S)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1129): 6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1130): 9-(4-(1-aminoethyl)phenyl)-6-ethynyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1131): (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1132): (R)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1133): 9-(4-(2-aminoethyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1134): 9-(4-(1-aminoethyl)phenyl)-8-(difluoromethyl)thieno[2,3-c]quinolin-4(5H)-one; (1135): (R)-6-bromo-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1136): 9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1137): 9-(4-butylphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1138): 9-(4-butylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1139): N-(2-chloroethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1140): 9-(4-((3-bromopyrrolidin-1-yl)sulfonyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1141): (S)-9-(4-(1-(methylsulfonamido)propyl)phenyl)-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-8-yl methanesulfonate; (1142): 9-(4-(2-aminoethyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1143): 9-(4-(3-(dimethylamino)-1-hydroxypropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1144): N-(2-bromoethyl)-4-(6-chloro-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1146): N-(2-bromoethyl)-4-(5-ethyl-8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1147): (S)-8-methoxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1148): (S)-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1149): 9-(4-(1-aminoethyl)phenyl)-8-(((2-hydroxyethyl)amino)methyl)thieno[2,3-c]quinolin-4(5H)-one; (1150): (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1151): (R)-9-(4-(1-(dimethylamino)propyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1152): 8-hydroxy-9-(4-pentylphenyl)thieno[2,3-c]quinolin-4(5H)-one; (1153): 9-(4-(2-aminoacetyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1154): (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1155): 8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1156): 8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1157): (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1158): (R)-9-(4-(1-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1159): (R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1160): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1161): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1162): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)butanenitrile; (1163): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1164): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1165): 6-chloro-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1166): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1167): 9-(4-(2-aminoethyl)-3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1168): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1169): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1170): 6-chloro-8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1171): 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1172): (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1173): 6-bromo-8-methoxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1174): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1175): (R)-9-(4-(1-aminopropyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1176): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1177): 9-(4-(2-aminoethyl)-3,5-difluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1178): 9-(4-(2-(dimethylamino)ethyl)-3,5-difluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1179): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1180): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6,7-dichloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1181): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1182): (S)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1183): 6-bromo-8-hydroxy-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1185): N-(2-hydroxyethyl)-4-(8-methoxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1186): methyl 3-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanoate; (1187): (R)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1188): (R)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1189): (R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1190): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1191): 9-(4-(2-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1192): 9-(4-(2-aminoethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1193): 9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1194): (S)-6-chloro-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1195): (S)-6-chloro-9-(4-(1-(diethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1196): (S)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1197): (S)-8-hydroxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1198): 4-(8-hydroxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-N-(2-hydroxyethyl)benzenesulfonamide; (1199): N-(2-bromoethyl)-4-(8-hydroxy-5-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1200): (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1201): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1202): 9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1203): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-2-(phenylsulfonyl)thieno[2,3-c]quinolin-4(5H)-one; (1204): N-(1-chloropropan-2-yl)-4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1205): N-(1-chloropropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide; (1206): 9-(4-(2-aminoethyl)-3-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1207): 9-(4-(2-aminoethyl)-3-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1208): 9-(4-(2-aminoethyl)-2-chloro-5-methoxyphenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1209): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1210): (R)-9-(4-(1-aminopropyl)phenyl)-8-hydroxy-5,6-dimethylthieno[2,3-c]quinolin-4(5H)-one; (1211): 9-(4-(2-aminoethyl)-2-chloro-5-hydroxyphenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1212): 9-(4-(aminomethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1213): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1214): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1215): (S)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1216): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1217): 9-(4-(2-aminoethyl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1218): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1219): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1220): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-cyclopropyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1221): 9-(4-(2-aminoethyl)-3-fluorophenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1222): (S)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1223): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1224): 9-(4-(2-aminoethyl)-2-bromo-5-hydroxyphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1225): (S)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1226): 3-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; (1227): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1228): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1229): 2-(2-fluoro-4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; (1230): 6-cyclopropyl-9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1231): 6-cyclopropyl-9-(4-(2-(dimethylamino)ethyl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1232): (S)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1233): (S)-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1234): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1235): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1236): 9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1237): 9-(4-(2-amino-1,1-dicyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1238): 3-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanenitrile; (1239): 9-(4-(2-amino-1-cyclopentylethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1240): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-cyclopropyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1241): 9-(4-(3-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1242): 9-(4-(2-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1243): 9-(4-(2-aminopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1244): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-cyclopropyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1245): 6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1246): 6-bromo-9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1247): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1248): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1249): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinoline-8-carbonitrile; (1250): (R)-9-(4-(1-aminoethyl)phenyl)-8-hydroxy-6-vinylthieno[2,3-c]quinolin-4(5H)-one; (1251): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1252): 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1253): 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1254): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1255): (R)-9-(4-(1-aminoethyl)phenyl)-6-ethyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1256): (R)-9-(4-(1-aminoethyl)phenyl)-6-(difluoromethyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1257): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1258): 9-(3-fluoro-4-(2-(methylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1259): 6-bromo-9-(4-(1-(dimethylamino)-2-methylpropan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1260): 9-(4-(1-amino-2-methylpropan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1261): 9-(4-(3-aminopropyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1262): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1263): 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1264): 9-(4-(2-aminoethyl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1265): (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1266): 9-(4-(2-aminopropyl)phenyl)-6-ethyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1267): (R)-9-(4-(1-aminoethyl)phenyl)-6-butyl-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1268): 9-(4-(2-aminoethyl)-3-chlorophenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1269): 9-(4-(2-aminopropyl)phenyl)-6-ethyl-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1270): 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-2-(oxetan-3-yl)acetonitrile; (1271): 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1272): (R)-6-ethyl-8-hydroxy-9-(4-(1-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1273): 9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1274): 9-(4-(1-amino-3-methylbutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1275): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1276): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1277): 9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1278): 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1279): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1280): 9-(4-(1-aminopropan-2-yl)-3-chlorophenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1281): 9-(4-(2-amino-2-methylpropyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1282): 9-(4-(2-amino-2-methylpropyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1283): 9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1284): 8-methoxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1285): 8-hydroxy-6-methyl-9-(4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1286): 9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1287): 9-(4-(1-amino-2-methylpropan-2-yl)-3-fluorophenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1288): 9-(4-(1-amino-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1289): 9-(4-(2-amino-2-methylpropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1290): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1291): 9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1292): 9-(4-(2-amino-2-methylpropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1293): 9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1294): 9-(3-fluoro-4-(3-methyl-1-(methylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1295): 9-(4-(1-(dimethylamino)-3-methylbutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1296): 9-(4-(1-(dimethylamino)-3-methylbutan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1297): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1298): (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1299): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1300): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1301): 8-methoxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1302): 8-hydroxy-6-methyl-9-(4-(piperidin-3-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1303): (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1304): (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1305): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1306): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1307): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1309): 9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1310): (S)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1311): (R)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1312): 9-(4-(1-aminobutan-2-yl)phenyl)-6-chloro-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1314): 9-amino-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1315): (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1316): (R)-9-(3-fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1317): (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1318): (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1319): (R)-9-(4-(1-aminopropan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1320): 9-((4-(2-aminoethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1321): 9-(4-(1-(aminomethyl)cyclobutyl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1324): (R)-9-(4-(1-(dimethylamino)propan-2-yOphenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1325): 9-((4-(aminomethyl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1326): 9-((4-(aminomethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1327): 9-((4-(1-aminopropan-2-yl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1328): 9-((4-(1-aminopropan-2-yl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1329): 9-(4-(2-aminopropan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1330): 9-(4-(2-aminopropan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1331): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1332): 9-(4-((R)-1-aminopropan-2-yl)phenyl)-8-hydroxy-2-(1-hydroxyethyl)thieno[2,3-c]quinolin-4(5H)-one; (1333): 9-(4-((R)-1-aminopropan-2-yephenyl)-2-(1-hydroxyethyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1334): 3-(4-((8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)amino)phenyl)propanenitrile; (1335): 9-((3-(2-aminoethyl)phenyl)amino)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1336): 9-((4-(2-aminoethyl)phenyl)amino)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1337): 9-(4-(2-(ethylamino)propyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1338): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1339): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1340): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-hydroxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one; (1341): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxy-2,6-dimethylthieno[2,3-c]quinolin-4(5H)-one; (1342): 9-(4-((R)-1-aminopropan-2-yl)phenyl)-2-(1-hydroxyethyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1343): 2-((4(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)amino)acetonitrile; (1344): (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1345): 9-(3-chloro-4-(2-(ethylamino)ethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1346): 9-(4-(3-((dimethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1347): (R)-6-chloro-9-(4-(1-(dimethylamino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1348): 9-(4-(2-(ethylamino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1349): 9-(4-(2-(ethylamino)ethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1350): 9-(4-(2-(ethyl(methyl)amino)propyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1351): 2-(hydroxy(piperidin-4-yl)methyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1352): (R)-9-(4-(1-aminobutan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1353): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1354): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-chloro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1355): 8-methoxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1356): 9-(4-(2-(ethyl(methyl)amino)ethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1357): 9-(4-(3-(aminomethyl)pentan-3-yl)phenyl)-6-chloro-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1358): 9-(4-(3-((dimethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1359): 9-(6-(dimethylamino)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1360): (R)-9-(4-(1-(dimethylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1361): (R)-8-methoxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1362): 9-(4-(3-((diethylamino)methyl)pentan-3-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1363): 9-(3-chloro-4-(2-(ethylamino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1364): 8-hydroxy-6-methyl-9-(4-(2-(methylamino)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1365): (R)-9-(4-(1-(dimethylamino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1366): (R)-9-(4-(1-(ethyl(methyl)amino)butan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1367): (R)-9-(4-(1-(diethylamino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1368): (R)-9-(4-(1-(ethyl(methyl)amino)butan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1369): 2-((4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino)acetonitrile; (1370): 2-((4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)(methyl)amino)acetonitrile; (1371): 9-(3-chloro-4-(2-(ethyl(methyl)amino)ethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1372): 9-(4-(1-((dimethylamino)methyl)cyclobutyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1373): (R)-9-(4-(1-aminopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1374): 9-(6-(2-aminoethoxy)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1375): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1376): 9-(6-(2-aminoethoxy)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1377): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1378): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1379): (R)-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1380): (R)-8-hydroxy-6-methyl-9-(4-(1-(methylamino)butan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1381): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1383): (R)-9-(4-(1-aminopropan-2-yl)phenyl)-2-fluoro-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1384): 9-(6-((2-aminoethyl)amino)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1385): 9-(6-((2-aminoethyl)amino)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1386): (S)-6-chloro-9-(4-(1-(ethyl(methyl)amino)propan-2-yl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1387): (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1388): (R)-9-(4-(1-(diethylamino)propan-2-yl)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1389): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1390): 9-(4-(1-amino-2,2,2-trifluoroethyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1391): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1392): (4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; (1393): 8-methoxy-6-methyl-9-(4-(2-(methylsulfinyl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1394): 8-hydroxy-6-methyl-9-(4-((methylsulfonyl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1395): (4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; (1396): 9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1397): (R)—N-(2-(2-fluoro-4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; (1398): (R)—N-(2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; (1399): (S)-9-(4-(1-(dimethylamino)propan-2-yl)-3-fluorophenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1400): 9-(4-((2-aminoethyl)(methyl)amino)phenyl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1401): 9-(4-(1-(aminomethyl)cyclopropyl)phenyl)-6-bromo-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1402): 2-(6-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-3-yl)acetonitrile; (1403): 8-hydroxy-6-methyl-9-(4-(2-(methylsulfinyl)ethyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1404): 8-methoxy-6-methyl-9-(4-((methylsulfonyl)methyl)phenyl)thieno[2,3-c]quinolin-4(5H)-one; (1405): 5-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)nicotinamide; (1406): 2-(5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)propanenitrile; (1407): 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanamide; (1408): 9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1409): 2-(5-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile; (1410): 2-hydroxy-2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide; (1411): N-(tert-butyl)-2-hydroxy-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide; (1412): 2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propanamide; (1413): 2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide; (1414): 9-(4-(2-amino-1-fluoroethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1415): 9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-hydroxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1416): 2-(5-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile; (1417): 2-(5-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile; (1418): 2-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)-2-methylpropanenitrile; (1419): 2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propane-1-sulfonamide; (1420): 9-(4-(2-amino-1-hydroxyethyl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one; (1421): 9-(6-(1-amino-2-methylpropan-2-yl)pyridin-3-yl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one; (1422): N-cyclopropyl-1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; (1423): 2-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)propanenitrile; (1424): (R)—N-(2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; (1425): N-ethyl-1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; (1426): 9-(6-(1-aminopropan-2-yl)pyridin-3-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one; (1427): N-cyclopropyl-1-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; (1428): 1-(5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)pyridin-2-yl)cyclopropanecarbonitrile; (1429): N-ethyl-1-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)methanesulfonamide; (1430): 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; (1431): 1-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethanesulfonamide; (1432): (R)—N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; (1433): (R)—N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide; (1434): (R)—N-(2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; (1435): (R)—N-(2-(4-(8-hydroxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)methanesulfonamide; (1436): (R)—N-(2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide; (1437): (R)—N-(2-(4-(8-hydroxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide; (1438): (R)—N-(2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl)-N-methylmethanesulfonamide; or a pharmaceutically acceptable salt thereof.
 13. A pharmaceutical composition comprising at least one compound of claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
 14. A method of killing a PBK dependent cancer cell in a subject in need thereof, comprising administering to said subject an effective amount of a compound or a pharmaceutically acceptable salt thereof of claim
 1. 